C‒C Coupling :: Wiley-VCH Hot Topics

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C–C Coupling
The development of metal-catalyzed cross-coupling reactions over the past 30 years
has revolutionized the way, carbon-carbon bonds between sp and sp2 carbon atoms
are formed. These methods have profoundly changed the protocols for theconstruction of natural products, building blocks for supramolecular chemistry andself-assembly, organic materials and polymers, and lead compounds in medicinal
chemistry from simpler entities. The 2010 Nobel prize in chemistry for E. Negishi, R.
Heck, and A. Suzuki underlines the importance of direct bond formation betweeen
carbon atoms.
Read the laureates' lectures:
Ei-ichi Negishi*
Magical Power of Transition Metals: Past, Present, and Future (Nobel Lecture)
Angew. Chem. 2011, 123, 6870–6897; Angew. Chem. Int. Ed. 2011, 50, 6738–6764
Akira Suzuki*
Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct C–C Bonds (Nobel Lecture)
Angew. Chem. 2011, 123, 6854–6869; Angew. Chem. Int. Ed. 2011, 50, 6722–6737
Find all articles on C–C coupling in Wiley Online Library...
Recent Articles
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Synthesis of Iron Oxide Palladium Nanoparticles and Their Catalytic Applications for Direct Coupling of Acyl
Chlorides with Alkynes
Creating new bonds: A new, magnetic, silica-based palladium nanocatalyst has beensynthesized and applied for the first time in the direct coupling of acyl chlorides withterminal alkynes to prepare a variety of ynones under copper-free, phosphine-free, andaerobic conditions at room temperature without relying on additives or inert conditions.
[Full Paper]
Rakesh K. Sharma, Manavi Yadav, Rashmi Gaur, Radhika Gupta, Alok Adholeya,Manoj B. Gawande
ChemPlusChem, September 30, 2016, DOI: 10.1002/cplu.201600321. Read article
Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation
A halo to make them shine: A
high-yielding nitroxyl-radical-catalyzed
oxidative coupling reaction between
amines protected with an electronwithdrawing group and silylated
nucleophiles proceeded through theactivation of N-halogenated amides by thenitroxyl-radical catalyst to give imines. The N-halogenated amide intermediates were generated in situ from amides bytreatment with a halogenation reagent (see scheme).
[Communication]
Katsuhiko Moriyama, Masako Kuramochi, Kozo Fujii, Tsuyoshi Morita, Hideo TogoAngew. Chem. Int. Ed., September 29, 2016, DOI: 10.1002/anie.201607223. Read article
Sequential Functionalization of Alkynes and Alkenes Catalyzed by Gold(I) and Palladium(II) N-HeterocyclicCarbene Complexes
Golden combination: The iodination of terminal alkynes using N-iodosuccinimide in the presence of a AuI-NHC (NHC=Nheterocyclic carbene) catalyst was achieved in good to excellent yields under mild reaction conditions. The resulting
1-iodoalkynes were used as organic building blocks for the synthesis of trisubstituted (Z)-fluoroalkenes in two sequential

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steps: The selective AuI-catalyzed hydrofluorination to yield (Z)-2-fluoro-1-iodoalkenes,
followed by a Suzuki–Miyaura cross-coupling with aryl boronic acids catalyzed by a
PdII-NHC complex.
[Full Paper]
Alberto Gómez-Herrera, Fady Nahra, Marcel Brill, Steven P. Nolan, Catherine S. J. Cazin
ChemCatChem, September 26, 2016, DOI: 10.1002/cctc.201600868. Read article

Generation of an 4-Isoxazolyl Anion Species: Facile Access to Multifunctionalized Isoxazoles
Taking position: Preparation of a 4-isoxazolyl anion
species from 4-iodoisoxazole using iPrMgCl⋅LiCl enabled
introduction of a wide variety of functional groups into the4-position of the isoxazole ring in good to excellent yields.
This approach provides various isoxazolyl metal species
which can be used for multifunctionalization of isoxazoles.
The step-by-step synthesis of 3,4,5-trisubstituted
isoxazoles was achieved by using the this 4-isoxazolyl anion method.
[Communication]
Taiki Morita, Shinichiro Fuse, Hiroyuki Nakamura
Angew. Chem. Int. Ed., September 26, 2016, DOI: 10.1002/anie.201608039. Read article
Surface-Functionalized Electrospun Titania Nanofibers for the Scavenging and Recycling of Precious Metal Ions
Must have the precious: Precious metals are widely used as catalysts in industry. It isof critical importance to keep the precious metal ions leached from catalysts at a level
below one part per million (ppm) in final products and to recycle the expensive metals.
Precious metal ions were scavenged by surface-functionalized electrospun TiO2
nanofibers and further recycled for use as catalysts. This system can be potentiallyapplied in pharmaceutical industry.
[Communication]
Yunqian Dai, Eric Formo, Haoxuan Li, Jiajia Xue, Younan Xia
ChemSusChem, September 23, 2016, DOI: 10.1002/cssc.201600787. Read article
Palladium(II)@Zirconium-Based Mixed-Linker Metal–Organic Frameworks as Highly Efficient and Recyclable
Catalysts for Suzuki and Heck Cross-Coupling Reactions
In the mix: It is possible to control the density of theintroduced active centers by adjusting the feed ratio of thelinkers that contain functional groups during the synthesis of
metal–organic frameworks. The prepared heterogeneous Pd
catalysts are very efficient for Suzuki and Heck cross-coupling
reactions with a very low Pd loading and could be recycled inat least 10 cycles.
[Full Paper]Rong Sun, Bing Liu, Bo-Geng Li, Suyun Jie
ChemCatChem, September 22, 2016, DOI:
10.1002/cctc.201600774. Read article[{Pd(µ-OH)Cl(IPr)}2] - a highly efficient precatalyst of Suzuki - Miyaura coupling, able to act also under base-freeconditions[Communication]
Sylwia Ostrowska, Jan Lorkowski, Maciej Kubicki, Cezary Pietraszuk
ChemCatChem, September 10, 2016, DOI: 10.1002/cctc.201600998. Read article
Phosphine-Catalyzed Direct δ-Carbon Addition of Alkynones to Electron-Deficient Carbonyl-Group-Containing
Compounds: Preparation of Conjugated Dienes
All about the δ Carbon: The unexplored δ-carbon of alkynones could be activated as a nucleophilic reaction site andtrapped by electron-deficient carbonyl-group-containing compounds upon phosphine catalysis, providing diverse δ-addition
and isomerization products in moderate to excellent yields.
[Full Paper]
Yao-Liang Sun, Xiao-Nan Zhang, Yin Wei, Min Shi
ChemCatChem, September 01, 2016, DOI: 10.1002/cctc.201600811. Read article

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Metal-Promoted Coupling Reactions Implying Ligand-Based Redox Changes
Ligand, camera, action! The advent of innovative (catalytic) pathways relying on
ligand-based redox events is reviewed in the context of coupling reactions. Thiscooperative approach between ligand and metal can offer attractive alternatives tothe classic two-electron catalytic cycles and foster new reactivities.
[Minireview]
Jérémy Jacquet, Marine Desage-El Murr, Louis Fensterbank
ChemCatChem, September 01, 2016, DOI: 10.1002/cctc.201600616. Read article

Synthesis and Optical Properties of meso-CF3-BODIPY with Acylethynyl Substituents in the 3-Position of theIndacene Core
Mechanoactivated BODIPY synthesis: BODIPY
chromophores, combining a meso-CF3 group andacylethynyl substituents in one molecule, weresynthesized for the first time. The key step is thesolid-phase mechanoactivated ethynylation ofmeso-CF3-dipyrromethanes by acylbromoacetylenesin Al2O3 or K2CO3 media.
[Full Paper]
Denis N. Tomilin, Konstantin B. Petrushenko, Lyubov N. Sobenina, Maxim D. Gotsko, Igor A. Ushakov, Anna D.
Skitnevskaya, Alexander B. Trofimov, Boris A.Trofimov
Asian J. Org. Chem., August 30, 2016, DOI: 10.1002/ajoc.201600303. Read article
Silver-Catalyzed Cross-Dehydrogenative Coupling (CDC) Strategy for the Construction of Dialkyl/Dibenzyl
Dibenzo[b,f][1,4]thia-/oxazepin-11-yl Phosphonates
Silver surfer: Medicinally important dialkyl/diaryl dibenzo[b,f][1,4]thiazepin-11-yl
phosphonates were synthesized by the atom-economical cross-dehydrogenative
coupling of dibenzothia-/oxazepines and dialkyl/diaryl phosphites.
[Full Paper]
Debasmita Saha, Tanpreet Kaur, Anuj Sharma
Asian J. Org. Chem., August 24, 2016, DOI: 10.1002/ajoc.201600283. Read article

Palladium-Catalyzed Suzuki–Miyaura Coupling Reactions of Boronic Acid Derivatives with Aryl Chlorides
Improved coupling reactions: A series of new
biphenyl N,P-monophosphine ligands L havebeen developed by introduction of two methoxy
groups to the biphenyl backbone. The ligands
were found to be much more effective than theircounterpart Buchwald ligands in Suzuki–Miyaura
coupling reactions of sterically hindered andelectron-rich aryl chlorides with aryl boronicacids. A variety of tri-ortho-substituted or tetra-ortho-substituted biaryls or hetero-biaryls were conveniently prepared in up
to 99 % yield by using L1-[Pd2(dba)3] (dba=dibenzylideneacetone) as the catalyst.
[Full Paper]
Zihong Zhou, Yaqi Zhang, Wang Xia, Huixuan Chen, Hao Liang, Xuefeng He, Sifan Yu, Rihui Cao, Liqin Qiu
Asian J. Org. Chem., August 16, 2016, DOI: 10.1002/ajoc.201600319. Read article
Structure-Defined 3D Nanocomposite Polymer Networks: Versatile Heterogeneous Catalytic Platforms in Organic
Synthesis
Structure-defined 3D catalytic nanocomposite polymer networks were synthesized based on monodisperse
polyvinylpyrrolidone (PVP)-stabilized Pd colloidal nanohybrids encapsulated within 1,2-bis-(2-iodoethoxy)ethane (BIEE)-3/6

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crosslinked poly(2-dimethylamino)ethyl methacrylate homopolymer networks. Thesematerials were evaluated as heterogeneous catalytic supports in Heck, SuzukiMiyaura and Sonogashira coupling reactions.
[Full Paper]
Andreas S. Kalogirou, Mariliz Achilleos, Constantina Procopiou, Eugenia Vasile,
Panayiotis A. Koutentis, Theodora Krasia-Christoforou
ChemistrySelect, July 18, 2016, DOI: 10.1002/slct.201600318. Read article

The Hiyama Cross-Coupling Reaction: New Discoveries
In this account recent developments in the Hiyama cross-coupling reaction from 2010
up today are presented. The most important methodology involves formation of biaryl
systems by using aryl bromides or iodides and aryl trialkoxy silanes: other variants arefar less studied.
[Personal Account]Francisco Foubelo, Carmen Nájera, Miguel Yus
The Chemical Record, July 14, 2016, DOI: 10.1002/tcr.201600063. Read article
Nickel-Catalyzed Borylation of Aryl and Benzyl 2-Pyridyl Ethers: A Method for Converting a Robust ortho-Directing
Group[Communication]
Mamoru Tobisu, Jiangning Zhao, Hirotaka Kinuta, Takayuki
Furukawa, Takuya Igarashi, Naoto ChataniAdv. Synth. Catal., June 2, 2016, DOI:
10.1002/adsc.201600336. Read article.

Iron-Catalyzed Cross-Coupling of 1-Alkynylcyclopropyl Tosylates and Related Substrates[Communication]
Daniel J. Tindall, Helga Krause, Alois FürstnerAdv. Synth. Catal., May 25, 2016, DOI:
10.1002/adsc.201600357. Read article.

Self-Assembled Multilayer-Stabilized Nickel Nanoparticle Catalyst for Ligand-Free Cross-Coupling Reactions: insitu Metal Nanoparticle and Nanospace Simultaneous Organization[Full Paper]
Naoyuki Hoshiya, Katsumasa Fujiki, Takahisa Taniguchi,
Tetsuo Honma, Yusuke Tamenori, Mincen Xiao, Nozomi
Saito, Mami Yokoyama, Akira Ishii, Hiromichi Fujioka, Satoshi
Shuto, Yoshihiro Sato, Mitsuhiro Arisawa
Adv. Synth. Catal., April 27, 2016, DOI:
10.1002/adsc.201600024. Read article.

Catalytic Efficiency of Primary β-Amino Alcohols and Their Derivatives in Organocatalysis
This review demonstrates the catalytic
efficiency of primary β-amino alcohols andtheir derivatives in organocatalysis. Thesesimple amino alcohols are inexpensivealternatives to other primary aminoorganocatalysts, being easy to synthesize
and air-stable and offering the potential for
introduction of different functional groups
and alteration of steric sites.
[Microreview]
Ummareddy Venkata Subba Reddy, Madhu
Chennapuram, Chigusa Seki, Eunsang
Kwon, Yuko Okuyama, Hiroto Nakano
Eur. J. Org. Chem., April 26, 2016, DOI: 10.1002/ejoc.201600164. Read article.
Discogens Possessing Aryl Side Groups Synthesized by Suzuki Coupling of Triphenylene Triflates and Their
Self-Organization Behavior

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Versatile Suzuki cross-coupling reactions between
arylboronic acids and triphenylenyl triflates generatea rich diversity of attractive functional discogens.
[Full Paper]
Ke-Qing Zhao, Yue Gao, Wen-Hao Yu, Ping Hu,
Bi-Qin Wang, Benoît Heinrich, Bertrand Donnio
Eur. J. Org. Chem., April 13, 2016, DOI:
10.1002/ejoc.201600270. Read article.

Water-Soluble C-Scorpionate Complexes – Catalytic and Biological Applications
Water-soluble carbon homoscorpionates and their coordination chemistry arereviewed. Moreover, the application of the resulting water-soluble tris(pyrazol1-yl)methane metal complexes as catalysts for C–C bond formation and oxidative
functionalization as well as their use as antiproliferative and antimicrobial agents are
addressed.
[Microreview]
Luísa M. D. R. S. Martins, Armando J. L. Pombeiro
Eur. J. Inorg. Chem., March 31, 2016, DOI: 10.1002/ejic.201600053. Read article.

Multicomponent Cascade Synthesis of Biaryl-Based Chalcones in Pure Water and in an Aqueous Micellar
Environment
The multicomponent cascade synthesis ofbiaryl-based chalcones was carried out inpure water and in an aqueous micellarsystem. The first step of the protocol was asimple Pd-catalysed, ligand-free, andaerobic Suzuki–Miyaura reaction inaqueous medium. The resulting
intermediates then underwent an in-situ
aldol condensation reaction to givebiaryl(hetero)chalcones in good to excellent yields.
[Full Paper]
Nicola Armenise, Danilo Malferrari, Sara Ricciardulli, Paola Galletti, Emilio Tagliavini
Eur. J. Org. Chem., March 2, 2016, DOI: 10.1002/ejoc.201600095. Read article.
Allylic C–H Activation of Olefins by a TpMe2IrIII Compound
The IrIII complex [TpMe2Ir(C6H5)2(N2)] [TpMe2 =hydridotris(3,5-dimethylpyrazolyl)borate] reacts
with different olefins to yield organometallic
compounds that derive from allylic C–H activationsin processes that also generate organic couplingproducts that involve the vinylic positions of theolefin.
[Full Paper]
Crispín Cristóbal, Laura L. Santos, Rubén
Gutiérrez-González, Eleuterio Alvarez, Margarita Paneque, Manuel L. Poveda
Eur. J. Inorg. Chem., January 19, 2016, DOI: 10.1002/ejic.201501253. Read article.
Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for
Trifluoromethylthiolation of Aryl Iodides
Efficient synthesis! A low cost method for the generation ofCuSCF3 by a triphenylphospine-mediated deoxygenative
reduction of Langloisʼ reagent (CF3SO2Na) has beendeveloped (see scheme). This method can be applied for theconvenient synthesis of a wide array of ligated and air-stable
CuSCF3 complexes. Additionally, the CuSCF3 complexes
generated in situ by this protocol were found totrifluoromethylthiolate (hetero)aryl iodides with high efficiency.

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[Communication]
Yi Yang, Long Xu, Siqi Yu, Xiaoqiang Liu, Yu Zhang, David A. Vicic
Chem. Eur. J., December 21, 2015, DOI: 10.1002/chem.201504790. Read article.
Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
Stairway to heaven? In a convergent synthesis of racemic
5-amino[6]hexahelicene (see figure), cross-coupling reactions assemble apentacyclic framework, with a metal-catalyzed ring closure as the final step. The
enantiomers are separated by means of chromatography and the absoluteconfigurations assigned by comparison of the CD spectra with hexahelicene.
Furthermore, scanning tunneling microscopy (STM) on Au(111) was performed
under ultrahigh vacuum.
[Full Paper]
Maarten W. van der Meijden, Edith Gelens, Natalia Murillo Quirós, Javier D. Fuhr,
J. Esteban Gayone, Hugo Ascolani, Klaus Wurst, Magalí Lingenfelder, Richard M.
Kellogg
Chem. Eur. J., December 14, 2015, DOI: 10.1002/chem.201502798. Read article.
Near-IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building
BlocksVersatile functionalization of the BODIPY core:
The borondipyrromethene (BODIPY) system has
been derivatized in a versatile manner through astrategy based on orthogonal reactivity (seefigure). This has allowed access to some red/NIRemitting dyes with superior properties to current
commercial laser dyes.
[Full Paper]
Cesar F. A. Gómez-Durán, Ixone Esnal, Ismael Valois-Escamilla, Arlette Urías-Benavides, Jorge Bañuelos, Iñigo
López Arbeloa, Inmaculada García-Moreno, Eduardo Peña-Cabrera
Chem. Eur. J., November 26, 2015, DOI: 10.1002/chem.201503090. Read article.
Direct Carboxylation of Aryl Tosylates by CO2 Catalyzed by In situ-Generated Ni0
Direct carboxylation of aryl tosylates by CO2 is rendered possible by a Ni0 catalyst,generated in situ by reduction of [NiBr2(bipy)] with manganese metal. This approach,which requires neither a glove-box nor the preparation of a sensitive organometallic
derivative, is applicable to a wide range of aromatic phenols, bearing either electrondonating or withdrawing substituents.
[Full Paper]
Fatima Rebih, Manuel Andreini, Aurélien Moncomble, Anne Harrison-Marchand,
Jacques Maddaluno, Muriel DurandettiChem. Eur. J., October 30, 2015, DOI: 10.1002/chem.201503926. Read article.

© Wiley-VCH 2015.

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