bluuebunny/crossref_metadata_2025 huggingface dataset:
ChemInform Abstract: Phenol and Aniline Oxidative Coupling with Alkenes by Using Hypervalent Iodine Dimer for the Rapid Access to Dihydrobenzofurans and Indolines.
Authors: Kita Yasuyuki , Dohi Toshifumi , Nakae Tomofumi , Toyoda Yosuke , Koseki Daichi , Kubo Hiroko , Kamitanaka Tohru
Published: April 2015

The highly reactive hypervalent iodine dimer [Ph(CF3COO)I]‐O‐[I(OCOCF3)Ph] is shown to promote the oxidative phenolic coupling with styrenes to afford different benzofuran derivatives.
ChemInform Abstract: An Unexpected 2,3‐Dihydrofuran Derivative Ring Opening Initiated by Electrophilic Bromination: Scope and Mechanistic Study.
Authors: Zhao Yi , Wong Ying‐Chieh , Yeung Ying‐Yeung
Published: April 2015

The novel ring opening reaction of dihydrofuran derivatives yields linear chain keto‐carboxylates, possibly influenced by moisture in the solvent.
ChemInform Abstract: TEMPO/NBu4Br‐Catalyzed Selective Alcohol Oxidation with Periodic Acid.
Authors: Attoui Mariam , Vatele Jean‐Michel
Published: April 2015

The reaction proceeds with primary and secondary alcohols forming aldehydes and ketones, resp.
ChemInform Abstract: Rhodium(III)/Copper(II)‐Promoted trans‐Selective Heteroaryl Acyloxylation of Alkynes: Stereodefined Access to trans‐Enol Esters.
Authors: Pham Manh V. , Cramer Nicolai
Published: April 2015

Benzofurans (I), furans (V) and thiophenes (VII) are regio‐ and trans‐selectively alkenylated at C2 by alkynes under Rh catalysis in the presence of copper(II) pivaloate.
ChemInform Abstract: Superstable Palladium(0) Complex as an Air‐ and Thermostable Catalyst for Suzuki Coupling Reactions.
Authors: Jakab Alexandra , Dalicsek Zoltan , Holczbauer Tamas , Hamza Andrea , Papai Imre , Finta Zoltan , Timari Geza , Soos Tibor
Published: April 2015

A novel tris(triphenylphosphine) Pd‐complex with unprecedented temperature and air‐stability is discovered and successfully used as catalyst for Suzuki coupling reactions of aryl bromides with aryl dioxaborolanes.
ChemInform Abstract: Nickel‐Catalyzed Direct Carboxylation of Olefins with CO2: One‐Pot Synthesis of α,β‐Unsaturated Carboxylic Acid Salts.
Authors: Limbach Michael , et al.
Published: April 2015

Numerous alkenes such as ethylene, styrenes, butadienes, and cyclic dienes form α,β‐unsaturated carboxylic acid salts in high yields and with high selectivities for the linear product.
ChemInform Abstract: Gold(I)‐Catalyzed, Stereocontrolled Enamide Synthesis from Primary Amides and Propargyl Aldehydes Using a Tandem Strategy.
Authors: Kim Sang Min , Lee Dabon , Hong Soon Hyeok
Published: April 2015

A wide range of enamides is prepared from primary amides and propargyl aldehydes by a Au(I)‐catalyzed tandem amide addition and Meyer—Schuster rearrangement.
ChemInform Abstract: A Simple One‐Pot Preparation of N‐Allenyl Amides, Ureas, Carbamates and Sulfonamides Using a DMSO/tBuOK Protocol.
Authors: Bousfield Thomas W. , Kimber Marc C.
Published: April 2015

The novel procedure is operationally simple, scalable, and provides various N‐allenyl derivatives.
ChemInform Abstract: Silver(I)‐Catalyzed Ring‐Contractive Rearrangement: A New Entry to 5‐Alkylidene‐2‐cyclopentenones.
Authors: Zhao Liang , Wang Jinlian , Zheng Hongyan , Li Yun , Yang Ke , Cheng Bin , Jin Xiaojie , Yao Xiaojun , Zhai Hongbin
Published: April 2015

The rearrangement of 6‐diazo‐2‐cyclohexenones is investigated and found to tolerate substrates bearing alkyl, alkenyl, and aryl substituents with a substituent in position 5 being essential for the formation of the desired products.
ChemInform Abstract: Preparation of Cycloheptane Ring by Nucleophilic Cyclopropanation of 1,2‐Diketones with Bis(iodozincio)methane.
Authors: Haraguchi Ryosuke , Takada Yoshiaki , Matsubara Seijiro
Published: April 2015

While performing the reactions under classical batch conditions requires thorough control of the reaction temperature to avoid side reactions, the latter are circumvented by continuous flow conditions, thus increasing the reaction yields.
ChemInform Abstract: N‐Heterocyclic Carbene‐Catalyzed α‐Alkylation of Ketones with Primary Alcohols.
Authors: Zhu Yanfang , Cai Chun , Lu Guoping
Published: April 2015

N‐Heterocyclic carbenes are used as efficient catalysts for the synthesis of dialkylated ketones.
ChemInform Abstract: Facile One‐Pot Synthesis of 4‐Substituted Semicarbazides.
Authors: Bogolubsky Andrey V. , Moroz Yurii S. , Mykhailiuk Pavel K. , Dmytriv Yurii V. , Pipko Sergey E. , Babichenko Liudmyla N. , Konovets Anzhelika I. , Tolmachev Andrey
Published: April 2015

4‐ Mono‐ and disubstituted semicarbazides (III) and (VI) (25 examples) in all are obtained starting from bis(2,2,2‐trifluoroethyl)carbonate or 2,2,2‐trifluoroethylchloroformate and primary and secondary alkyl‐ and arylamines under conditions of parallel synthesis.
ChemInform Abstract: Recyclable and Reusable Pd(OAc)2/P(1‐Nap)3/[bmim] [PF6]/H2O System for the Addition of Arylboronic Acids to Aldehydes.
Authors: Zhao Hong , Cheng Mingzhu , Zhang Tinli , Cai Mingzhong
Published: April 2015

The catalytic system can be reused six times without significant loss of catalytic activity.
ChemInform Abstract: BF3·Et2O‐Catalyzed One‐Pot Synthesis of N,N′‐(2‐Alkyl‐1,3‐diarylprop‐1‐ene‐1,3‐diyl)diacetamides Through a Tandem Aldol—Double Ritter‐Type Reaction.
Authors: Kasthuri Mahesh , Nakka Srinuvasu , Babu H. Sharath , Sudhakar Ch. , Venkatanarayana M. , Kumar P. V. Nagendra
Published: April 2015

A hitherto not described multicomponent tandem aldol‐double Ritter‐type reaction for the atom economic construction of multifunctional diacetamides (III) (12 examples) is developed.
ChemInform Abstract: The Direct Electrophilic Cyanation of β‐Keto Esters and Amides with Cyano Benziodoxole.
Authors: Wang Yao‐Feng , Qiu Jiashen , Kong Dejie , Gao Yongtao , Lu Feipeng , Karmaker Pran Gopal , Chen Fu‐Xue
Published: April 2015

The developed method is applicable to cyclic β‐ketoesters, but not to acyclic ones.
ChemInform Abstract: Facile Synthesis of Spiro Chromanone‐Tetrahydrothiophenes with Three Contiguous Stereocenters via Sulfa‐Michael/Aldol Cascade Reactions.
Authors: Hu Ya‐Jian , Wang Xiao‐Bing , Li Su‐Yi , Xie Sai‐Sai , Wang Kelvin D. G. , Kong Ling‐Yi
Published: April 2015

The triethylamine catalyzed reaction of chromanones with dithianediols affords the title compounds in excellent yields with high diastereoselectivities.
ChemInform Abstract: Copper‐Catalyzed Regioselective Synthesis of Furan via Tandem Cycloaddition of Ketone with an Unsaturated Carboxylic Acid under Air.
Authors: Ghosh Monoranjan , Mishra Subhajit , Monir Kamarul , Hajra Alakananda
Published: April 2015

The operationally simple preparation of 2,3,5‐trisubstituted furans succeeds upon the reaction of aryl alkyl ketones, 2‐phenylacetophenone, and various cyclic ketones with cinnamic acid derivatives, but fails using alkyl methyl ketones or crotonic acid.
ChemInform Abstract: A Convenient Synthesis of 3,4‐cis‐Disubstituted Pyrrolidin‐2‐ones.
Authors: Arfaoui Aicha , Saadi Fatma , Ben Smida Youssef , Arfaoui Youssef , Nefzi Adel , Amri Hassen
Published: April 2015

The highly stereoselective synthesis of the title compounds is realized through conjugate addition of amines to substrate (I) followed by a 5‐exo‐trig cyclization process.
ChemInform Abstract: Unusually Efficient Deformylative Synthesis of 1,2,8,9‐Tetrasubstituted Dipyrrins from 4,5‐Disubstituted Pyrrole‐2‐carbaldehydes.
Authors: Oda Mitsunori , Fujiwara Yurie , Kumai Yoshimitsu , Ohta Akira , Miyatake Ryuta
Published: April 2015

The dipyrrins (IV) obtained show a clear color change from red to blue when exposed to Broensted acids.
ChemInform Abstract: Transfer of Aryl Halide to Alkyl Halide: Reductive Elimination of Alkylhalide from Alkylpalladium Halides Containing syn‐β‐Hydrogen Atoms.
Authors: Hao Wei , Wei Junnian , Geng Weizhi , Zhang Wen‐Xiong , Xi Zhenfeng
Published: April 2015

Unsymmetrical alkynes (VIII) react regioselectively to yield compounds (IX).
ChemInform Abstract: The Cycloaddition of 2‐Phenylamino‐1‐azaazulene with Diphenylacetylene Using Palladium Catalytic Systems.
Authors: Fujii Hiroyuki , Oka Shigeki , Nakamura Ippei , Kawai Yu , Ikeda Reiko , Konakahara Takeo , Abe Noritaka
Published: April 2015

The cycloaddition reaction of 2‐phenylamino‐1‐azaazulene (I) or the corresponding bromo derivative (VI) with diphenylacetylene (II) under various reaction conditions is studied.
ChemInform Abstract: Stereoselective Synthesis of 1,2‐Diamine Containing Indolines by a Conjugate Addition Nitro‐Mannich Reaction.
Authors: Anderson James C. , Campbell Ian B. , Campos Sebastien , Shannon Jonathan , Tocher Derek A.
Published: April 2015

Electron‐rich aryl bromides are found to be reluctant to cyclize.
ChemInform Abstract: Fe‐Promoted Radical Cyanomethylation/Arylation of Arylacrylamides to Access Oxindoles via Cleavage of the sp3 C—H of Acetonitrile and the sp2 C—H of the Phenyl Group.
Authors: Pan Changduo , Zhang Honglin , Zhu Chengjian
Published: April 2015

The operationally simple reaction procedure tolerates a variety of functional groups.
ChemInform Abstract: Base‐Catalyzed Cyclization of Ugi‐Adducts to Substituted Indolyl Based γ‐Lactams.
Authors: Shiri Morteza , Mirpour‐Marzoni Seyedeh Zeinab , Bozorgpour‐Savadjani Zahra , Soleymanifard Bita , Kruger Hendrik G.
Published: April 2015

The condensation of 2‐formylindole (I), 3‐chloropropanoic acid (II), isocyanides (III), and various amines (IV) leads to the Ugi adducts (V) which undergo post‐condensation cyclization in the presence of K2CO3 to form a series of novel substituted γ‐lactams (VI).
ChemInform Abstract: Synthesis of Functionalized Cyanopyrazoles via Magnesium Bases.
Authors: Dishington Allan , Feron J. Lyman , Gill Kathryn , Graham Mark A. , Hollingsworth Ian , Pink Jennifer H. , Roberts Andrew , Simpson Iain , Tatton Matthew
Published: April 2015

Tetramethylpiperidinylmagnesium chloride lithium chloride is used for the sequential deprotonation of N‐silyl‐protected 4‐methylpyrazole and subsequent functionalization by first cyanation in position 3 and then arylation in position 5.
ChemInform Abstract: Efficient 4,5‐Dihydro‐1H‐imidazol‐5‐one Formation from Amidines and Ketones under Transition‐Metal Free Conditions.
Authors: Xie Yanjun , Cheng Xiufang , Liu Saiwen , Chen Hui , Zhou Wang , Yang Luo , Deng Guo‐Jun
Published: April 2015

Title compounds [(III), (V), (VII), and (IX)] are catalyst‐free under base‐promotion synthesized starting from readily available materials.
ChemInform Abstract: Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via C—N Bond Formation.
Authors: Gao Pin , Li Hong‐Xia , Hao Xin‐Hua , Jin Dong‐Po , Chen Dao‐Qian , Yan Xiao‐Biao , Wu Xin‐Xing , Song Xian‐Rong , Liu Xue‐Yuan , Liang Yong‐Min
Published: April 2015

The scalable iron‐catalyzed aerobic oxidative reaction is influenced by the steric hindrance of the substrates′ aryl substituents.
ChemInform Abstract: Potassium Iodide and Ammonium Nitrate Catalyzed Aerobic Oxidative Cyclization of Ketones with Thioureas in Ionic Liquid: An Access to 2‐Aminothiazoles.
Authors: Zhao Jinwu , Xu Jingxiu , Chen Jiaxi , He Minghua , Wang Xiaoqin
Published: April 2015

A wide range of ketones and thioureas undergo the transformation to the corresponding 2‐aminothiazole heterocycles.
ChemInform Abstract: Transition‐Metal‐Free Oxidative Iodination of 1,3,4‐Oxadiazoles.
Authors: Dannenberg Carl Albrecht , Bizet Vincent , Zou Liang‐Hua , Bolm Carsten
Published: April 2015

An experimentally simple procedure for the oxidative iodination of 1,3,4‐oxadiazoles (I) and the related thiadiazole (III) is developed using NaI as iodine source and Selectfluor as oxidant.
ChemInform Abstract: Preparation of 5‐Substituted 1H‐Tetrazoles Catalyzed by Scandium Triflate in Water
Authors: Coca Adiel , Turek Evan , Feinn Liana
Published: April 2015

[via [2 + 3] cycloaddition of sodium azide with nitriles].
ChemInform Abstract: N,N′‐Dioxide/Nickel(II)‐Catalyzed Asymmetric Inverse‐Electron‐Demand Hetero‐Diels—Alder Reaction of β,γ‐Unsaturated α‐Ketoesters with Enecarbamates.
Authors: Zhou Yuhang , Zhu Yin , Lin Lili , Zhang Yulong , Zheng Jianfeng , Liu Xiaohua , Feng Xiaoming
Published: April 2015

N,N′‐Dioxide/nickel(II) complexes are developed to catalyze the inverse‐electron‐demand hetero‐Diels—Alder reaction of β,γ‐unsaturated α‐ketoesters with acyclic enecarbamates.
ChemInform Abstract: An Efficient Domino Sonogashira/Double Carbopalladation/C—H‐Activation Reaction Leading to Fluorescent Polycyclic Aromatic Hydrocarbons.
Authors: Tietze Lutz F. , Eichhorst Christoph
Published: April 2015

Six polycyclic fluorescent aromatic hydrocarbons of type (III) are prepared by a domino reaction.
ChemInform Abstract: Domino Reaction of 2,2‐Dihydroxyindene‐1,3‐dione with Aromatic Amines: Efficient Synthesis of Isochromeno[4,3‐b]indol‐5(11H)‐one Derivatives.
Authors: Meng Xiao‐Yan , Sun Mu‐Yan , Zhao Fu‐Jie , Dang Yi‐Jing , Jiang Bo , Tu Shu‐Jiang
Published: April 2015

The reaction proceeds with excellent regioselectivity.
ChemInform Abstract: Copper‐Catalyzed Regioselective Cross‐Dehydrogenative Coupling of Coumarins with Benzylic Csp3‐H Bonds.
Authors: Zhou Shi‐Liu , Guo Li‐Na , Duan Xin‐Hua
Published: April 2015

Optimized conditions allow the synthesis of 3‐benzylcoumarins in moderate to good yields.
ChemInform Abstract: Synthesis of Aminonaphthopyranones and Aminonaphthochromenones by Blaise‐Reaction‐Initiated Cascade Procedures.
Authors: He Yan , Zhang Xinying , Fan Xuesen
Published: April 2015

A convenient one‐pot protocol allows the preparation of the title species via a tandem reaction of benzonitrile derivatives with a Reformatsky reagent generated in situ from Zn and ethyl bromoacetate.
ChemInform Abstract: Chroman‐4‐ones via Microwave‐Promoted Domino Claisen Rearrangement—Oxa‐Michael Addition: Synthesis of Tabchromones A and B.
Authors: Schmidt Bernd , Riemer Martin , Schilde Uwe
Published: April 2015

Compound (VI) can be easily transformed into tabchromone A (VII) and B (VIII).
ChemInform Abstract: Synthesis of 1‐Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2‐Alkynylbenzaldoximes with Isocyanoacetates.
Authors: Wang Tao , Li Rou , Yu Danhong , Gu Chenghao , Xiong Fei , Chen Zhiyuan
Published: April 2015

The reaction generally succeeds for substrates with aryl and alkyl substituted alkynyl moieties, but fails in case of terminal, tert‐butyl, or trimethylsilyl substituted alkynyl groups.
ChemInform Abstract: Facile Preparation of 1,2‐Dihydroisoquinolines from N‐Benzylsulfonamides and Bromoacetylenes.
Authors: Urabe Hirokazu , Yamagishi Masahito , Ishii Azusa , Hata Takeshi
Published: April 2015

Optimum reaction conditions are examined for the synthesis of the title compounds from N‐benzylsulfonamides (I) and bromoacetylenes (II).
ChemInform Abstract: Efficient Merging of Copper and Photoredox Catalysis for the Asymmetric Cross‐Dehydrogenative‐Coupling of Alkynes and Tetrahydroisoquinolines.
Authors: Perepichka Inna , Kundu Soumen , Hearne Zoe , Li Chao‐Jun
Published: April 2015

The report constitutes the first example for a highly efficient asymmetric cross‐dehydrogenative coupling in between tertiary amines, namely tetrahydroisoquinolines, and terminal alkynes.
ChemInform Abstract: Enantioselective Epoxidation of Dihydroquinolines by Using Iminium Salt Organocatalysts.
Authors: Bulman Page Philip C. , Day David P. , Chan Yohan
Published: April 2015

The epoxidation of dihydroquinolines (I) in the presence of optically active iminium salt catalyst gives epoxides with low to moderate enantioselectivities.
ChemInform Abstract: Iron‐Catalyzed C—H Bond Functionalization for the Exclusive Synthesis of Pyrido[1,2‐a]indoles or Triarylmethanols.
Authors: Karthikeyan Iyyanar , Sekar Govindasamy
Published: April 2015

Selective iron‐catalyzed C‐H activation of 2‐benzylhydrylpyridine renders possible the formation of pyridoindoles via an intramolecular C‐H amination reaction.
ChemInform Abstract: Rhodium(III)‐Catalyzed One‐Pot Access to Isoquinolines and Heterocycle‐Fused Pyridines in Aqueous Medium Through C—H Cleavage.
Authors: Zhang Jitan , Qian Hongsheng , Liu Zhanxiang , Xiong Chunhua , Zhang Yuhong
Published: April 2015

A variety of ketones and internal alkynes are converted into isoquinolines and heterocyclic fused pyridines.
ChemInform Abstract: Direct Arylation of Imidazo[1,5‐a]azines Through Ruthenium and Palladium Catalysis.
Authors: Sustac Roman Daniela , Poiret Valentin , Pelletier Guillaume , Charette Andre B.
Published: April 2015

The imidazo[1,5‐a]azine system is described as directing group for site‐selective Ru‐catalyzed C‐H arylation at the ortho‐position with aryl halides as coupling partners.
ChemInform Abstract: H8‐BINOL Chiral Imidodiphosphoric Acids Catalyzed Enantioselective Synthesis of Dihydroindolo‐/‐pyrrolo[1,2‐a]quinoxalines.
Authors: Fan Yan‐Sen , Jiang Yi‐Jun , An Dong , Sha Di , Antilla Jon C. , Zhang Suoqin
Published: April 2015

The scalable method relies on a Pictet‐Spengler reaction between indolyl anilines and ketones or aldehydes catalyzed by a newly developed H8‐BINOL‐based imidodiphosphoric acid providing the products in high yields and with excellent enantioselectivities.
ChemInform Abstract: Concise Synthesis of Tetrazole‐Ketopiperazines by Two Consecutive Ugi Reactions.
Authors: Zarganes‐Tzitzikas Tryfon , Patil Pravin , Khoury Kareem , Herdtweck Eberhardt , Doemling Alexander
Published: April 2015

The synthesis of a range of diversely substituted tetrazole‐fused ketopiperazines is achieved through Ugi‐tetrazole synthesis with ester substituted isonitriles (III) followed by ester hydrolysis and UGI 4CR reaction.
ChemInform Abstract: Synthesis of 2,7‐Disubstituted 5,10‐Diaryl‐5,10‐dihydrophenazines via Iron‐Catalyzed Intramolecular Ring‐Closing C—H Amination.
Authors: Nakamura Masaharu , Aoki Yuma , Imayoshi Ryuji , Hatakeyama Takuji , Takaya Hikaru
Published: April 2015

Optimum reaction conditions are examined for the intramolecular ring closing C—N bond formation affording six 5,10‐diaryl‐5,10‐dihydrophenazines of type (II).They can find potential use as hole‐injection materials in organic electroluminescence devices.
ChemInform Abstract: Stereoselective Synthesis of cis‐2,6‐Disubstituted Morpholines and 1,4‐Oxathianes by Intramolecular Reductive Etherification of 1,5‐Diketones.
Authors: Gharpure Santosh J. , Anuradha Dandela , Prasad Jonnalagadda V. K. , Srinivasa Rao Pidugu
Published: April 2015

A triethylsilane/TmsOTf‐mediated reductive etherification is developed to allow the cyclization of diketones of type (I) and (III) to give 2,6‐disubstituted morpholines and 1,4‐oxathianes in excellent trans‐diastereoselectivity.
ChemInform Abstract: Gold(I)‐Catalyzed Synthesis of Cyclic Sulfamidates: Current Scope, Stereochemistry and Competing Ene‐Allene Cycloisomerization.
Authors: Higginbotham Mari C. M. , Kennedy Lorna , Lindsay Anita G. , Troester Andreas , Bebbington Magnus W. P.
Published: April 2015

The first gold‐catalyzed preparation of cyclic sulfamidates, leading to a range of unusually substituted and sterically hindered products under mild conditions is reported.
ChemInform Abstract: A Rare Type of Sesquiterpene and β‐Santalol Derivatives from Santalum album and Their Cytotoxic Activities.
Authors: Matsuo Yukiko , Sakagami Hiroshi , Mimaki Yoshihiro
Published: April 2015

8 New compounds (I)‐(VIII) are isolated from the heartwood of Santalum album together with 4 known compounds.
ChemInform Abstract: A New Bis‐seco‐Abietane Diterpenoid from Hyptis crenata Pohl ex Benth.
Authors: Yun Young Sook , Fukaya Haruhiko , Nakane Takahisa , Takano Akihito , Takahashi Shigeru , Takahashi Yuji , Inoue Hideshi
Published: April 2015

The new bis‐seco‐abietane diterpenoid named hyptisolide A (I) is isolated from the methanolic extracts of the aereal parts of Hyptis crenata Pohl ex Benth.
ChemInform Abstract: Cytotoxic (9βH)‐Pimarane and (9βH)‐17‐Norpimarane Diterpenes from the Tuber of Icacina trichantha.
Authors: Monday Onakpa Michael , Zhao Ming , Goedecke Tanja , Chen Wei‐Lun , Che Chun‐Tao , Santarsiero Bernard D. , Swanson Steven M. , Uzoma Asuzu Isaac
Published: April 2015

One new (9βH)‐pimarane, 17‐hydroxyicacinol (I), is isolated together with two known (9βH)‐pimaranes and two known (9βH)‐17‐norpimaranes.
ChemInform Abstract: Synthesis of Antibacterial 1,3‐Diyne‐Linked Peptoids from an Ugi‐4CR/Glaser Coupling Approach.
Authors: Brauer Martin C. N. , Neves Filho Ricardo A. W. , Westermann Bernhard , Heinke Ramona , Wessjohann Ludger A.
Published: April 2015

A library of dimeric peptoids [ct.(VI)] are chemoselectively obtained by Ugi four‐component reaction followed by a copper‐catalyzed alkyne homocoupling (Glaser reaction).
ChemInform Abstract: A New Flavonol Glycoside from the Leaves of Boscia senegalensis.
Authors: Morgan Abubaker M. A. , Kim Jang Hoon , Kim Sang Kyum , Lim Chi‐Hwan , Kim Young Ho
Published: April 2015

A new flavonol glycoside, bosenegaloside A, is isolated along with seven known compounds from Boscia senegalensis.
ChemInform Abstract: Palladium(0)‐Catalyzed Synthesis of Cyclic Glucosides.
Authors: Huang Xin , Fu Chunling , Ma Shengming
Published: April 2015

O‐Acetyl protected allenyl β‐D‐glucoside reacts with aryl, hetaryl, and alkenyl iodides in a highly regio‐ and stereoselective manner, and the products are deacetylated to ten‐membered cyclic glycosides.
ChemInform Abstract: The Application of Formyl Group Activation of Bromopyrrole Esters to Formal Syntheses of Lycogarubin C, Permethyl Storniamide A and Lamellarin G Trimethyl Ether.
Authors: Gupton John T. , Telang Nakul , Patteson Jon , Lescalleet Kristin , Yeudall Scott , Sobieski John , Harrison Andrew , Curry Will
Published: April 2015

The natural products lycogarubin (I), permethyl storniamide A (II), and lamellarin G trimethyl ether (III) are interesting biological active compounds.
ChemInform Abstract: Sequential Sonagashira and Larock Indole Synthesis Reactions in a General Strategy to Prepare Biologically Active β‐Carboline‐Containing Alkaloids.
Authors: Pan Xiaohong , Bannister Thomas D.
Published: April 2015

The two palladium‐mediated title processes serve as key steps for the synthesis of various β‐carboline‐containing natural products.
ChemInform Abstract: Total Synthesis of Acetylcholinesterase Inhibitor Macakurzin C.
Authors: Lee Dongjoo , Shin Iljin , Ko Eunjae , Lee Kiyoun , Seo Seung‐Yong , Kim Hyoungsu
Published: April 2015

The concise synthesis of macakurzin C in nine steps is presented.
ChemInform Abstract: γ‐Lactonic and Linear Carboxylic Acids from Cultured Lichen Mycobionts of Graphis scripta
Authors: Tanahashi Takao , Hamada Nobuo , Takenaka Yukiko
Published: April 2015

isolation and characterization of new carboxylic acids (I)—(III)
ChemInform Abstract: New Isoprenylated Xanthones from Cudrania tricuspidata.
Authors: Lei Chun , Liu Chang‐Chang , Pi En‐Hao , Hou Ai‐Jun
Published: April 2015

isolation and structure elucidation of new isoprenylated xanthones, cudratricusxanthones N (I), O (II), and P (III) along with five known compounds
ChemInform Abstract: Isolation and Biomimetic Synthesis of (.+‐.)‐Calliviminones A and B, Two Novel Diels—Alder Adducts, from Callistemon viminalis.
Authors: Kong Lingyi , et al.
Published: April 2015

Compounds (I) and (II) exhibit moderate inhibition on NO production on LPS‐activated RAW 264.0 cells.
ChemInform Abstract: 3‐epi‐Waol A and Waol C: Polyketide‐Derived γ‐Lactones Isolated from the Endophytic Fungus Libertella blepharis F2644.
Authors: Adames Itzel , Ortega Humberto E. , Asai Yumi , Kato Masaki , Nagaoka Kazuya , TenDyke Karen , Shen Young Yongchun , Cubilla‐Rios Luis
Published: April 2015

3‐epi‐Waol A (I) exhibits growth inhibition against the parasite Trypanosoma cruzi (IC50=22.71 μM), and against MCF‐7 (IC50=22.46 μM), HCT116 (IC50=6.2 μM), and H460 (IC50=1.0 μM) cancer cell lines.
ChemInform Abstract: The Chemistry of the Octahydrotriborate Anion [B3H8]‐
Authors: Bykov A. Yu. , Zhizhin K. Yu. , Kuznetsov N. T.
Published: April 2015

Review: 97 refs.
ChemInform Abstract: The Synthesis and Properties of Bimetallic D‐π Electron Systems Containing Metallocenyl Substituents of Fe or Ru, and π‐Electron Spacers of Heavier Main Group Elements from Group 14 or 15
Authors: Sasamori Takahiro
Published: April 2015

Review: 73 refs.
ChemInform Abstract: Coordination and Reactivity of Functionalized Fullerenes, Open‐Cage Fullerenes, and Endohedral Metallofullerenes by Organometallic Complexes
Authors: Yeh Wen‐Yann
Published: April 2015

Review: 117 refs.
ChemInform Abstract: Post‐Functionalization of Metal‐NHC Complexes: A Useful Toolbox for Bioorganometallic Chemistry (And Beyond)?
Authors: Cisnetti Federico , Gibard Clementine , Gautier Arnaud
Published: April 2015

Review: 109 refs.
ChemInform Abstract: Energy Cascades, Excited State Dynamics, and Photochemistry in Cob(III)alamins and Ferric Porphyrins
Authors: Rury Aaron S. , Wiley Theodore E. , Sension Roseanne J.
Published: April 2015

Review: 56 refs.
ChemInform Abstract: Bistren Cryptands and Cryptates: Versatile Receptors for Anion Inclusion and Recognition in Water
Authors: Alibrandi Giuseppe , Amendola Valeria , Bergamaschi Greta , Fabbrizzi Luigi , Licchelli Maurizio
Published: April 2015

Review: [46 refs.
ChemInform Abstract: Pyridine Synthesis by [4 + 2] Cycloadditions of 1‐Azadienes: Hetero‐Diels—Alder and Transition Metal‐Catalyzed Approaches
Authors: Neely Jamie M. , Rovis Tomislav
Published: April 2015

Review: 41 refs.
ChemInform Abstract: Synthesis and Biology of Cyclic Imine Toxins, an Emerging Class of Potent, Globally Distributed Marine Toxins
Authors: Stivala Craig E. , Benoit Evelyne , Araoz Romulo , Servent Denis , Novikov Alexei , Molgo Jordi , Zakarian Armen
Published: April 2015

Review: 151 refs.
ChemInform Abstract: Catalytic Enantioselective Organic Transformations via Visible Light Photocatalysis
Authors: Wang Chengfeng , Lu Zhan
Published: April 2015

Review: 79 refs.
ChemInform Abstract: Advances in Metal‐Assisted Non‐Electrophilic Fluoroalkylation Reactions of Organic Compounds
Authors: Lantano Beatriz , Torviso M. Rosario , Bonesi S. M. , Barata‐Vallejo S. , Postigo Al
Published: April 2015

Review: 146 refs.
ChemInform Abstract: Synthesis, Reactions and Applications of Pyranotriazolopyrimidines
Authors: Abd El‐Wahab Ashraf Hassan Fekry , Radini Ibrahim Ali , Mohamed Hany Mostafa
Published: April 2015

Review: 72 refs.
ChemInform Abstract: Synthesis of Side Chain N,N′‐Diaminoalkylated Derivatives of Basic Amino Acids for Application in Solid‐Phase Peptide Synthesis
Authors: Pitteloud Jean‐Philippe , Bionda Nina , Cudic Predrag
Published: April 2015

Review: 65 refs.
ChemInform Abstract: Backbone Amide Linker Strategy: Protocols for the Synthesis of C‐Terminal Peptide Aldehydes
Authors: Shelton Pernille Tofteng , Jensen Knud J.
Published: April 2015

Review: 22 refs.
ChemInform Abstract: Hydroxycarbazoles as Starting Materials in Organic Syntheses
Authors: Padmaja Pannala , Reddy Narayana
Published: April 2015

Review: 63 refs.
ChemInform Abstract: Comparison of Experimental and Calculated Chiroptical Spectra for Chiral Molecular Structure Determination
Authors: Polavarapu Prasad L. , Covington Cody L.
Published: April 2015

Review: 40 refs.
ChemInform Abstract: Understanding Cancer and the Anticancer Activities of Naphthoquinones — A Review
Authors: Wellington Kevin W.
Published: April 2015

Review: [276 refs.
ChemInform Abstract: Design of Protein Crystals in the Development of Solid Biomaterials
Authors: Abe Satoshi , Ueno Takafumi
Published: April 2015

Review: functionalization for applications in preparation of inorganic materials, asymmetric catalysis and accumulation of functional compounds; 67 refs.
ChemInform Abstract: Chemistry and Anticarcinogenic Mechanisms of Glycoalkaloids Produced by Eggplants, Potatoes, and Tomatoes
Authors: Friedman Mendel
Published: April 2015

Review: 141 refs.
ChemInform Abstract: The Structural Basis for Specificity in Lipoxygenase Catalysis
Authors: Newcomer Marcia E. , Brash Alan R.
Published: April 2015

Review: 52 refs.
ChemInform Abstract: Building with Bubbles: The Formation of High Surface Area Honeycomb‐Like Films via Hydrogen Bubble Templated Electrodeposition
Authors: Plowman Blake J. , Jones Lathe A. , Bhargava Suresh K.
Published: April 2015

Review: [116 refs.
ChemInform Abstract: Fluorescent Thiophene‐Based Materials and Their Outlook for Emissive Applications
Authors: Rasmussen Seth C. , Evenson Sean J. , McCausland Casey B.
Published: April 2015

Review: [128 refs.
ChemInform Abstract: Computational Organic Chemistry: Bridging Theory and Experiment in Establishing the Mechanisms of Chemical Reactions
Authors: Cheng Gui‐Juan , Zhang Xinhao , Chung Lung Wa , Xu Liping , Wu Yun‐Dong
Published: April 2015

Review: [186 refs.
Malignant risk stratification of thyroid FNA specimens with indeterminate cytology based on molecular testing
Authors: Paskaš Svetlana , Janković Jelena , Živaljević Vladan , Tatić Svetislav , Božić Vesna , Nikolić Aleksandra , Radojković Dragica , Savin Svetlana , Cvejić Dubravka
Published: April 2015

BACKGROUND

Fine‐needle aspiration (FNA) has been employed for many years for examining thyroid nodules, and the cytology of aspirates is the primary determinant for whether thyroidectomy is indicated. Fifteen to thirty percent of thyroid nodules, not being clearly benign or malignant, fall into an indeterminate category. The main goals of molecular diagnostics for thyroid nodules are to prevent unnecessary surgery in patients with benign nodules and to stop patients with malignant nodules from being subjected to repeated operations.

METHODS

This study was designed to evaluate the diagnostic utility of 4 markers in thyroid FNA cytology via testing for the BRAF V600E mutation and the expression of microRNA‐221, microRNA‐222, and galectin‐3 protein in FNA samples with indeterminate cytology.

RESULTS

A predictor model distinguishing benign samples from malignant samples on the basis of the 4 aforementioned markers was formulated. This decision model provided a sensitivity of 73.5%, a specificity of 89.8%, and a diagnostic accuracy of 75.7%. The positive predictive value was 80.6%, and the negative predictive value was 85.5%; this suggested that the prediction had good reliability.

CONCLUSIONS

One hundred twenty FNA samples were examined, and 62 nodules were classified as benign with the proposed diagnostic algorithm. This resulted in a reduction of the initial 120 patients to 58 and thus decreased by half the number of persons undergoing surgery. Cancer (Cancer Cytopathol) 2015;123:471–9. © 2015 American Cancer Society.
Fe K‐Edge X‐ray Absorption Fine Structure Determination of γ‐Al2O3‐Supported Iron‐Oxide Species
Authors: Tomita Atsuko , Miki Takeshi , Tango Takeru , Murakami Tatsuro , Nakagawa Hideyuki , Tai Yutaka
Published: April 2015

The structure of FeOx species supported on γ‐Al2O3 was investigated by using Fe K‐edge X‐ray absorption fine structure (XAFS) and X‐ray diffraction (XRD) measurements. The samples were prepared through the impregnation of iron nitrate on Al2O3 and co‐gelation of aluminum and iron sulfates. The dependence of the XRD patterns on Fe loading revealed the formation of α‐Fe2O3 particles at an Fe loading of above 10 wt %, whereas the formation of iron‐oxide crystals was not observed at Fe loadings of less than 9.0 wt %. The Fe K‐edge XAFS was characterized by a clear pre‐edge peak, which indicated that the FeO coordination structure deviates from central symmetry and that the degree of FeOFe bond formation is significantly lower than that in bulk samples at low Fe loading (<9.0 wt %). Fe K‐edge extended XAFS oscillations of the samples with low Fe loadings were explained by assuming an isolated iron‐oxide monomer on the γ‐Al2O3 surface.
Redefining Outcome Measurement: A Model for Brief Psychotherapy
Authors: McGuinty Everett , Nelson John , Carlson Alain , Crowther Eric , Bednar Dina , Foroughe Mirisse
Published: April 2015

Context

The zeitgeist for short‐term psychotherapy efficacy has fundamentally shifted away from evidence‐based practices to include evidence‐informed practices, resulting in an equally important paradigm shift in outcome measurement designed to reflect change in this short‐term modality.

Objective

The present article delineates a short‐term psychotherapy structure which defines four fundamental stages that all brief therapies may have in common, and are represented through Cognitive Behavioral Therapy, Solution‐Focused Brief Therapy, Narrative Therapy, and Emotion‐Focused Therapy.

Method

These four theoretical approaches were analyzed via a selected literature review through comparing and contrasting specific and common tasks as they relate to the process of psychotherapy and change. Once commonalities were identified within session, they were categorized or grouped into themes or general stages of change within the parameters of a four to six session model of short‐term therapy. Commonalities in therapeutic stages of change may more accurately and uniformly measure outcome in short‐term work, unlike the symptom‐specific psychometric instruments of longer‐term psychotherapy.

Results

A systematic framework for evaluating the client and clinician adherence to 20 specific tasks for these four short‐term therapies is presented through the newly proposed, Brief Task Acquisition Scale (BTAS). It is further proposed that the client–clinicians' adherence to these tasks will track and ultimately increase treatment integrity.

Conclusion

Thus, when the client–clinician relationship tracks and evaluates the three pillars of (1) stage/process change, (2) task acquisition, and (3) treatment integrity, the culmination of these efforts presents a new way of more sensitively measuring outcome in short‐term psychotherapy. Data collection is suggested as a first step to empirically evaluate the testable hypotheses suggested within this current model. Copyright © 2015 John Wiley & Sons, Ltd.

Key Practitioner Message

The clinician practitioner will note that the proposed Brief Services model removes the subjectivity of client satisfaction as a reliable outcome measure, and relies upon client and therapist adherence to specific tasks and stages of change within and across short‐term psychotherapy.

The clinical significance of the BTAS for the practitioner is three fold. The psychometric instrument (1) tracks stage or process change, (2) guides task acquisition, and (3) incorporates greater treatment integrity unlike other outcome measures.

The BTAS present a new way of conceptualizing change in short‐term psychotherapy regardless of modality or presenting issue, making it a more flexible and usable instrument for the clinician.

The BTAS may measure outcome more sensitively and accurately, thus offering the client, therapist and client‐therapist more information regarding change at each stage and at the end of short‐term psychotherapy.
Development and validation of an ESI‐LC‐MS/MS method for simultaneous identification and quantification of 24 analytes of forensic relevance in vitreous humour, whole blood and plasma
Authors: Arora Beauty , Velpandian Thirumurthy , Saxena Rohit , Lalwani Sanjeev , Dogra T. D , Ghose Supriyo
Published: April 2015

Detection and quantification of drugs from various biological matrices are of immense importance in forensic toxicological analysis. Despite the various reported methods, development of a new method for the detection and quantification of drugs is still an active area of research. However, every method and biological matrix has its own limitation, which further encourage forensic toxicologists to develop new methods and to explore new matrices for the analysis of drugs. In this study, an electrospray ionization‐liquid chromatograph‐tandem mass spectrometry (ESI‐LC‐MS/MS) method is developed and validated for simultaneous identification and quantification of 24 drugs of forensic relevance in various body fluids, namely, whole blood, plasma and vitreous humour. The newly developed method has been validated for intra‐day and inter‐day accuracy, precision, selectivity and sensitivity. Absolute recovery shows a mean of 84.5, 86.2, and 103% in the vitreous humour, whole blood and plasma respectively, which is suitable for the screening procedure. Further, the absolute matrix effect (AME) shows a mean of 105, 96.5, and 109% in the vitreous humour, whole blood and plasma, respectively. In addition, to examine the practical utility of this method, it has been applied for screening of drugs in post‐mortem samples of the vitreous humour, whole blood and plasma collected at autopsy from ten cadavers. Experimental results show that the newly developed method is well applicable for screening of analytes in all the three matrices. Copyright © 2015 John Wiley & Sons, Ltd.
Who's Pulling the Fracking Strings? Power, collaboration and Colorado fracking policy
Authors: Cook Jeffrey J.
Published: April 2015

Scholars have looked towards collaborative governance as one means to resolve complex environmental issues and this has travelled to the administrative policy realm in the form of negotiated rulemaking or more recently shuttle diplomacy. What is missing from this administrative literature, and that of collaborative governance literature more generally, is a discussion of the role of power in these processes. This paper provides a case study of the Colorado Oil and Gas Conservation Commission's (COGCC) collaborative rule‐making, the Statewide Groundwater Baseline Sampling and Monitoring Rule, to serve as a launch point to evaluate the role of power in state‐level collaborative processes. This research provides original interview data from agency staff and stakeholders to explore the ability of certain groups to exercise the power of agenda control to influence the outcome of the process in the controversial fracking arena. Here, the governor and agency staff were important in defining the problem, but determining the available solutions was more open to privileged stakeholders, namely industry. The interviewees suggested that these dynamics carry over to other COGCC rule‐makings and as such future scholars should evaluate the agenda control strategies of these groups to better understand why collaborative policy‐making, especially in the administrative realm, unfolds as it does. Copyright © 2015 John Wiley & Sons, Ltd and ERP Environment
Determinants of submaximal exercise capacity in patients at risk for heart failure with preserved ejection fraction—results from the DIAST‐CHF study
Authors: Stahrenberg Raoul , Duvinage André , Mende Meinhard , Gelbrich Götz , auf der Heide Wiebke , Düngen Hans‐Dirk , Binder Lutz , Nolte Kathleen , Herrmann‐Lingen Christoph , Hasenfuß Gerd , Pieske Burkert , Wachter Rolf , Edelmann Frank
Published: April 2015

Objectives and Background

The aim of this study was to identify determinants of submaximal exercise capacity as measured by 6 min walking distance in patients at risk for heart failure with preserved ejection fraction (HFpEF).

Methods

A cross‐sectional analysis from the prospective cohort programme Prevalence and Clinical Course of Diastolic Dysfunction and Heart Failure (DIAST‐CHF) that included a total of 1937 patients (age, 50–85 years) with >1 risk factor (hypertension, atherosclerotic disease, diabetes mellitus, and obstructive sleep apnoea) was carried out. Besides comprehensive clinical phenotyping, standardized 6 min walk test and state‐of‐the‐art echocardiography were performed, and blood samples for biomarker assessment were obtained. Patients with an ejection fraction <50% or without evaluable exercise test were excluded from this analysis.

Results

One thousand three hundred eighty‐seven patients fulfilled all criteria for this analysis. In the univariate analysis, 6 min walk distance was inversely related to E/e′ values (P < 0.001). In the multivariate analysis, 6 min walk distance decreased significantly with age, female sex, increasing body mass index, diabetes, chronic obstructive lung disease, and peripheral artery disease. However, the association of 6 min walk distance with resting parameters of diastolic function was significantly attenuated with multivariate regression. In contrast, mid‐regional pro‐adrenomedullin, mid‐regional pro‐atrial natriuretic peptide, and N‐terminal pro‐B‐type natriuretic peptide were independently associated with submaximal exercise capacity when added to the base model (all P < 0.001).

Conclusions

Classical risk factors for heart failure and neuroendocrine activation are independently associated with sub‐maximal exercise capacity, while diastolic function parameters obtained at rest were not. This observation substantiates the role of co‐morbidities as relevant contributors to the clinical picture of HFpEF and the limitation of resting indices of diastolic function for diagnosing HFpEF.
Syntheses of Ir4(CO)6(η5‐C5Me4H)2 and Ir7(μ3‐CO)3(CO)12(η5‐C5Me5) from Pentametallic Molybdenum‐Iridium Cluster Precursors
Authors: Fu Junhong , Randles Michael D. , Criddle Alan L. , Moxey Graeme J. , Schwich Torsten , Stranger Robert , Cifuentes Marie P. , Humphrey Mark G.
Published: April 2015

Reaction of Mo2Ir3(μ‐CO)3(CO)6(η5‐C5H5)2(η5‐C5Me5) with Ir(CO)2(η5‐C5Me4H) afforded the four‐valence‐electron‐deficient butterfly cluster Ir4(CO)6(η5‐C5Me4H)2; its stability has been rationalized with the aid of density functional theory calculations, which suggest that significant additional intracluster bonding alleviates the formal electron deficiency. Reaction of MoIr4(CO)10(η5‐C5H5)(η5‐C5Me5) with [N(PPh3)2][Ir(CO)4] afforded the capped octahedral cluster Ir7(μ3‐CO)3(CO)12(η5‐C5Me5), which possesses three semi‐face‐capping CO ligands. These outcomes demonstrate that heterometallic clusters may serve as a potential source of new homometallic clusters following appropriate M–M′ cleavage.
Continuous high power ultrasound treatment before malaxation, a laboratory scale approach: Effect on virgin olive oil quality criteria and yield
Authors: Bejaoui Mohamed Aymen , Beltrán Gabriel , Sánchez‐Ortiz Araceli , Sánchez Sebastian , Jiménez Antonio
Published: April 2015

Continuous application of high power ultrasound (HPU) on olive paste previous to malaxation at laboratory scale for virgin olive oil (VOO) extraction and its effect on process yield and the VOO quality have been studied. For the VOO samples, we determined the quality indices (free acidity value, peroxide value, K232, K270), bitterness, volatile composition, phenolic content (total and biophenols), tocopherol content, and pigments.

The application of ultrasound induced a quick heating of the paste from 20 to 28°C. The sonication treatment improved the industrial oil yield by 1% and the oil extractability by 5.74%. Moreover the HPU treatment did not cause changes in the quality indices, fatty acid composition and volatile aromatic compounds of the VOO. Furthermore the fat autoxidation process was not accelerated by this treatment. Meanwhile oil obtained from olive pastes treated with HPU showed higher content of tocopherol, chlorophylls and carotenoids whereas a reduction in phenolic content and bitterness index was observed.

Practical applications: The high power ultrasound (HPU) treatment of olive paste, before malaxation during the virgin olive oil (VOO) elaboration process, can improve the oil extraction yield without alteration of its quality parameters. The olive paste instantaneous heating observed with the HPU can allow the reduction of the malaxation step duration. The results obtained nowadays at laboratory scale are promising for the possibility of the continuous HPU treatment introduction in the olive oil elaboration process as aid or alternative to the malaxation. For this purpose further experiment at pilot and industrial scale are needed.

Continuous application of high power ultrasound before malaxation and its effect on the oil extractability and virgin olive oil characteristics.
Branched chain fatty acids concentrate prepared from butter oil via urea adduction
Authors: Mudgal Samriddh , Ran‐Ressler Rinat R. , Liu Lei , Brenna J. Thomas , Rizvi Syed S. H.
Published: April 2015

Saturated branched chain fatty acids (BCFA) intake in the US is greater than that of other bioactive fatty acids (FA), yet little information is available on methodologies to concentrate them. We report here the effect of urea‐to‐FA (urea:FA) ratio, adduction time, and temperature on the enrichment of branched chain fatty acids (BCFA) from butter oil. Urea adducts precipitate both saturated and monounsaturated hydrocarbon chains as urea complexes, leaving solubilized polyunsaturated FA and BCFA in the non‐urea adduct fraction (NUA). The optimum urea:FA ratio was found to be 4:1 and the optimum temperature to be 4°C. Adduction time had negligible effect on BCFA enrichment. Anteiso‐15:0 was most enriched across major BCFA under all conditions of temperature, time, and urea:FA ratio studied. In our preferred embodiment, a two‐stage urea adduction procedure applied to hydrolyzed butter oil resulted in an enrichment from <2% BCFA in the starting oil to >11% BCFA, indicating an enrichment factor of >6. The best method has a first stage performed at 4°C and urea:FA ratio of 4:1, and a second stage at 30°C and lower urea:FA ratio (2:1). Overall yield of BCFA in enriched fraction was about 10% of starting BCFA for two stages.

Practical applications: BCFA are constituents of the GI tract of healthy newborns and are known to prevent necrotizing enterocolitis. The average per capita BCFA intake of Americans is estimated to be about 220 mg/day from dairy whereas based on the current dietary recommendations of USDA it should be about 400 mg/day from dairy alone with total amounting to 575 mg/day including beef. Using the results of the current study, enriched BCFA concentrates can be prepared to meet the demand.

Enrichment in major branched chain fatty acids (BCFA) of butter oil after two stage urea adduction. First stage (NUA‐1) and second stage (NUA‐2) were conducted using 4:1; 4°C 2 h and 2:1, 30°C 2 h of urea‐to‐fatty acids ratio (wt/wt), temperature and time of adduction, respectively.
Stille Cross‐Coupling for the Functionalization of the Imidazole Backbone: Revisit, Improvement, and Applications of the Method
Authors: Sandtorv Alexander H. , Törnroos Karl Wilhelm , Bjørsvik Hans‐René
Published: April 2015

We have revisited the Stille coupling reaction for the functionalization of the imidazole backbone. In this context CuI was exploited as a co‐catalyst, which resulted in significantly improved yields of target coupling products. Furthermore, a systematic investigation of the effect of the auxiliary group on the N‐1‐ring atom was performed. When mono‐coupling is desired, the Tosyl (Tos) group is superior to the (dimethylamino)sulfonyl (DMAS) group, furnishing the corresponding 4‐coupled imidazoles in significantly higher yields. However, when bis‐coupling is preferred, the DMAS group is imperative for success of the coupling procedure. Utilizing this reaction protocol, we were successfully able to demonstrate the first examples of Stille bis‐coupling utilizing N‐DMAS‐4,5‐diiodoimidazole as substrate.