Naohiko Yoshikai
Professor
Graduate School of Pharmaceutical Sciences, Tohoku University
6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan
Phone/Fax: +81-22-795-6812/+81-22-795-6811
E-mail: naohiko.yoshikai.c5@tohoku.ac.jp
URL: http://www.pharm.tohoku.ac.jp/~sekkei/
Education
2005
Ph.D. (Chemistry)
Department of Chemistry, The University of Tokyo (Advisor: Prof. Eiichi Nakamura)
2002
M.Sc. (Chemistry)
Department of Chemistry, The University of Tokyo
2000
B.Sc. (Chemistry)
Department of Chemistry, The University of Tokyo
Professional Experience
2021.4–Present
Professor
Graduate School of Pharmaceutical Sciences, Tohoku University
2016.9–2021.3
Associate Professor (tenured)
Division of Chemistry and Biological Chemistry, School of Physical andMathematical Sciences, Nanyang Technological University
2009.7–2016.8
Assistant Professor
Division of Chemistry and Biological Chemistry, School of Physical andMathematical Sciences, Nanyang Technological University
2009.7–2014.6
Research Fellow
Singapore National Research Foundation (NRF)
2005.2–2009.6
Assistant Professor
Department of Chemistry, The University of Tokyo
2002.4–2005.2
JSPS Young Research Fellow
Research Interests
Novel organic reaction chemistry toward efficient synthesis and new chemical spaces
Awards2022
Mukaiyama Award
2020
Tokyo Chemical Industry (TCI)–Singapore National Institute of Chemistry (SNIC)
Industry Award in Synthetic Chemistry
2015
Asian Core Program Lectureship (from Thailand)
2014
Chemical Society of Japan Award for Young Chemists
2014
Asian Core Program Lectureship (from China and Korea)
2011
Asian Core Program Lectureship (from Japan)
2011
Thieme Chemistry Journal Award
2007
Inoue Research Award for Young Scientists

Publications
Journal Publications and Preprints
155.
Sasaki, S.; Kikuchi, J.; Ito, S.; Yoshikai, N. Stereoselective Approach toMultisubstituted Enolates from Unactivated Alkynes: Oxyalkylidenation of Alkynyl
Ketone Enolates with Aldehydes. J. Org. Chem. 2023, 88, 14096-14104.
154.
Tsukiji, K.; Hayakawa, T.; Kanemoto, K.; Yoshikai, N. Zinc-MediatedDiastereoselective Annulation of Cyclopropanols with Alkylidenemalononitriles via
Enolized Homoenolate. Asian J. Org. Chem. 2023, e202300114 [Prof. Keiji Maruoka’s
70th birthday collection].
153.
Saito, Y.; Kikuchi, J.; Wang, C.; Yoshikai, N. Site-Selective C–H Alkenylation of
N-Heteroarenes by Ligand-Directed Co/Al and Co/Mg Cooperative Catalysis. Angew.
Chem. Int. Ed. 2023, 62, e202301006.
152.
Yoshikai, N. Exploring New Reactions and Syntheses of Trivalent Iodine Compounds.
J. Synth. Org. Chem. Jpn. 2022, 80, 1011-1018.
151.
Kikuchi, J.; Maesaki, K.; Sasaki, S.; Wang, W.; Ito, S.; Yoshikai, N. Stereoselective
Synthesis of β-Alkoxy-β-amido Vinylbenziodoxoles via Iodo(III)etherification of
Ynamides. Org. Lett. 2022, 24, 6914-6918.
150.
Tsukiji, K.; Sekiguchi, Y.; Kanemoto, K.; Yoshikai, N. Diastereoselective Conversion of
Cyclopropanols to Cyclopentane-1,3-diols via Aldol Dimerization of Zinc
Homoenolates. Chem. Lett. 2022, 51, 1012-1014.
149.
Kikuchi, J.; Yoshikai, N. Cobalt Selectively Annulates. Nat. Synth. 2022, 1, 674-675(News & Views).
148.
Wang, C.-S.; Yu, Y.; Sunada, Y.; Wang, C.; Yoshikai, N. Cobalt-Catalyzed Carbo- andHydrocyanation of Alkynes via C–CN Bond Activation. ACS Catal. 2022, 12,4054-4066.
147.
Sekiguchi, Y.; Yoshikai, N. Zinc-Mediated Hydroxyallylation of Aldehydes with
Cyclopropanols: Direct Access to anti-sec,tert-Diols via Enolized Homoenolate. Org.
Lett. 2022, 24, 960-965 (Preprint: Sekiguchi, Y.; Yoshikai, N. ChemRxiv 2021, DOI:
DOI 10.26434/chemrxiv-2021-swc95).
146.
Chai, J.; Ding, W.; Wang, C.; Ito, S.; Wu, J.; Yoshikai, N. Ritter-Type Iodo(III)amidationof Unactivated Alkynes for the Stereoselective Synthesis of Multisubstituted
Enamides. Chem. Sci. 2021, 12, 15128-15133 (Preprint: Chai, J.; Ding, W.; Ito, S.; Wu,
J.; Yoshikai, N. ChemRxiv 2021, DOI: 10.33774/chemrxiv-2021-c2ftp.).
145.
Sekiguchi, Y.; Yoshikai, N. Zinc-Catalyzed β-Functionalization of Cyclopropanols via
Enolized Homoenolate. J. Am. Chem. Soc. 2021, 143, 18400-18405 (Preprint:
Sekiguchi, Y.; Yoshikai, N. ChemRxiv 2021, DOI: 10.33774/chemrxiv-2021-4jlsp).
144.
Sekiguchi, Y.; Lee, Y. Y.; Yoshikai, N. Nickel-Catalyzed Ring-Opening Allylation of
Cyclopropanols via Homoenolate. Org. Lett. 2021, 23, 5993-5997.
143.
Sekiguchi, Y.; Yoshikai, N. Enantioselective Conjugate Addition of Catalytically
Generated Zinc Homoenolate. J. Am. Chem. Soc. 2021, 143, 4775-4781 (Preprint:
Sekiguchi, Y.; Yoshikai, N. ChemRxiv 2021, DOI: 10.26434/chemrxiv.13607438.v1).
142.
Wang, C.-S.; Sun, Q.; Garcia, F.; Wang, C.; Yoshikai, N. Robust Cobalt Catalyst for
Nitrile/Alkyne [2+2+2] Cycloaddition: Synthesis of Polyarylpyridines and Their
Mechanochemical Cyclodehydrogenation to Nitrogen-Containing Polyaromatics.
Angew. Chem. Int. Ed. 2021, published online (Preprint: Wang, C.-S.; Sun, Q.; Garcia,
F.; Wang, C.; Yoshikai, N. ChemRxiv 2021, DOI: 10.26434/chemrxiv.13465697.v1)

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Laskar, R. A.; Ding, W.; Yoshikai, N. Iodo(III)-Meyer-Schuster Rearrangement of
Propargylic Alcohols Promoted by Benziodoxole Triflate. Org. Lett. 2021, 23,1113-1117.
Sekiguchi, Y.; Yoshikai, N. Metal-Catalyzed Transformations of Cyclopropanols via
Homoenolates. Bull. Chem. Soc. Jpn. 2021, 1, 265-280.
Xu, W.; Wu, M.; Yoshikai, N. Iron-Catalyzed Remote C-H Alkylation of
8-Amidoquinolines with Cycloalkanes. Synthesis 2020, published online.
Chai, J.; Ding, W.; Wu, J.; Yoshikai, N. Fluorobenziodoxole-BF3 Reagent for
Iodo(III)etherification of Alkynes in Ethereal Solvent. Chem. Asian J. 2020, 15,2166-2169.
Ding, W.; Wang, C.; Tan, J. R.; Ho, C. C.; León, F.; García, F.; Yoshikai,
N. Site-selective aromatic C-H λ3-iodanation with cyclic iodine(III) electrophile insolution and solid phases. Chem. Sci. 2020, 11, 7356-7361.
Yang, J.; Mori, Y.; Yamanaka, M.; Yoshikai, N. Cobalt-Catalyzed Intramolecular
Hydroacylation Involving Cyclopropane Cleavage. Chem. Eur. J. 2020, 26,
8302-8307.
Ding, W.; Chai, J.; Wang, C.; Wu, J.; Yoshikai, N. Stereoselective Access to Highly
Substituted Vinyl Ethers via trans-Difunctionalization of Alkynes with Alcohols andIodine(III) Electrophile. J. Am. Chem. Soc. 2020, 142, 8619-8624 (Preprint: Ding, W.;
Chai, J.; Wu, J.; Yoshikai, N. ChemRxiv 2020, DOI: 10.26434/chemrxiv.11770092.v1.)
Wang, C.-S.; Di Monaco, S.; Thai, A. N.; Wang, C.; Yoshikai, N. Cobalt/Lewis Acid
Catalysis for Hydrocarbofunctionalization of Alkynes via Cooperative C–H Activation.
ChemRxiv 2020, DOI: 10.26434/chemrxiv.11760519.v1.
Rahman, M. S.; Yoshikai, N. Synthesis of Triphenylene-Fused Phosphole Oxides via
C–H Functionalizations. Beilstein J. Org. Chem. 2020, 16, 524-529.
Laskar, R. A.; Yoshikai, N. Cobalt-Catalyzed, N–H Imine-Directed Arene C–H
Benzylation with Benzyl Phosphates. J. Org. Chem. 2019, 84, 13172-13178.
Ding, W.; Ho, Y. K. T.; Okuda, Y.; Wijaya, C. K.; Tan, Z. H.; Yoshikai, N.
Cobalt-Catalyzed Hydroacylative Dimerization of Allenes Leading to Skipped Dienes.
Org. Lett. 2019, 21, 6173-6178.
Sun, Q.; Yoshikai, N. Cobalt-Catalyzed Tandem Radical Cyclization/C–C Coupling
Initiated by Directed C–H Activation. Org. Lett. 2019, 21, 5238-5242.
Rahman, M. S.; Yoshikai, N. Synthesis and Properties of Phospha[5]helicenes
Bearing Inner-Rim Phosphorus Center. Org. Lett. 2019, 21, 5238-5242.
Yang, J.; Sekiguchi, Y.; Yoshikai, N. Cobalt-Catalyzed Enantioselective andChemodivergent Addition of Cyclopropanols to Oxabicyclic Alkenes. ACS Catal. 2019,
9, 5638-5644.
Wu, J.; Deng, X.; Yoshikai, N. Stereocontrolled Synthesis of Halovinylbenziodoxoles
via Hydro- and Iodochlorination of Ethynylbenziodoxoles. Chem. Eur. J. 2019, 25,7839-7842.
Xu, W.; Yoshikai, N. Iron‐Catalyzed ortho C−H Arylation and Methylation of
Pivalophenone N−H Imines. ChemSusChem 2019, 12, 3049-3053.
Yan, J.; Rahman, M. S.; Yoshikai, N. Pd‐Catalyzed Annulation of
1‐Halo‐8‐arylnaphthalenes and Alkynes Leading to Heptagon‐Embedded Aromatic
Systems, Chem. Eur. J. 2019, DOI: 10.1002/chem.201805746.
Yang, J.; Sun, Q.; Yoshikai, N. Cobalt-Catalyzed Regio- and Diastereoselective
Formal [3+2] Cycloaddition between Cyclopropanols and Allenes. ACS Catal. 2019, 9,
1973-1978.
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Ding, W.; Yoshikai, N. Cobalt-Catalyzed Intermolecular [2+2] Cycloaddition between
Alkynes and Allenes. Angew. Chem. Int. Ed. 2019, 58, 2500-2504.
Ding, W.; Ho, C. C.; Yoshikai, N. Photosensitized, Energy-Transfer-MediatedCyclization of 2-(1-Arylvinyl)benzaldehydes to Anthracen-9-(10H)-ones. Org.
Lett. 2019, 21, 1202-1206.
Yoshikai, N. Recent Advances in Enantioselective C-C Bond Formation via
Organocobalt Species. Synthesis 2019, 51, 135-145.
Yang, J.; Shen, Y.; Lim, Y. J.; Yoshikai, N. Divergent ring-opening coupling between
cyclopropanols and alkynes under cobalt catalysis. Chem. Sci. 2018, 9, 6928-6934.
Sun, Q.; Yoshikai, N. Cobalt-catalyzed directed ortho-methylation of arenes withmethyl tosylate. Org. Chem. Front. 2018, 7, 2214-2218.
Wu, C.; Yoshikai, N. Cobalt-Catalyzed Intramolecular Reactions between aVinylcyclopropane and an Alkyne: Switchable [5+2] Cycloaddition and Homo-Ene
Pathways. Angew. Chem. Int. Ed. 2018, 57, 6558-6562.
Xu, W.; Pek, J. H.; Yoshikai, N. Iron-Catalyzed Directed C–H Silylation of
Pivalophenone N–H Imines. Asian J. Org. Chem. 2018, 14, 1351-1354.
Xu, W.; Yoshikai, N. Cobalt-Catalyzed Directed C–H Alkenylation of Pivalophenone
N–H Imine with Alkenyl Phosphates. Beilstein J. Org. Chem. 2018, 14, 709-715.
Sun, Q.; Yoshikai, N. Cobalt-Catalyzed C(sp2)–H/C(sp3)–H Coupling via Directed C–
H Activation and 1,5-Hydrogen Atom Transfer. Org. Chem. Front. 2018, 5, 582-585.
Tan, W. W.; Wu, B.; Wei, Y.; Yoshikai, N. Copper and Secondary Amine-Catalyzed
Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes. Org.
Synth. 2018, 95, 1-14.
Xu, W.; Yoshikai, N. Cobalt-Catalyzed, N–H Imine-Directed Hydroarylation of
Styrenes. Org. Lett. 2018, 20, 1392-1395.
Lee, P.-S.; Xu, W.; Yoshikai, N. Directed C–H Alkenylation of Aryl Imines with Alkenyl
Phosphates Promoted by a Cobalt–N-Heterocyclic Carbene Catalyst. Adv. Synth.
Catal. 2017, 359, 4340-4347 (Very Important Paper).
Yan, J.; Yoshikai, N. Phenanthrene Synthesis via Chromium-Catalyzed Annulationof 2-Biaryl Grignard Reagents and Alkynes. Org. Lett. 2017, 19, 6630-6633.
Wu, B.; Wu, J.; Yoshikai, N. Benziodoxole Triflate as a Versatile Reagent for
Iodo(III)cyclization of Alkynes. Chem. Asian J. 2017, 12, 3123-3127.
Yoshikai, N. Iron-Catalyzed C–C Bond Formation via Chelation-Assisted C–H
Activation. Isr. J. Chem. 2017, 57, 1117-1130.
Yan, J.; Yoshikai, N. Chromium-Catalyzed Migratory Arylmagnesiation of
Unactivated Alkynes. Org. Chem. Front. 2017, 4, 1972-1975.
Xu, W.; Yoshikai, N. Pivalophenone Imine as a Benzonitrile Surrogate for Directed
C–H Bond Functionalization. Chem. Sci. 2017, 8, 5299-5304.
Yoshikai, N.; Santra, M.; Wu, B. Synthesis of Donor-Acceptor-Type
Benzo[b]phosphole and Naphtho[2,3-b]phosphole Oxides and Their Solvatochromic
Properties. Organometallics 2017, 20, 1392-1395.
Tan, W. W.; Ong, Y. J.; Yoshikai, N. Synthesis of Highly Substituted Pyridines
through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines.
Angew. Chem. Int. Ed. 2017, 56, 8240-8244.
Wu, B.; Melvina; Wu, X.; Yeow, E. K. L.; Yoshikai, N. Versatile Telluracyclc
Synthesis via the Sequential Electrophilic Telluration of C(sp2)–Zn and C(sp2)–H
Bonds. Chem. Sci. 2017, 8, 4527-4532.
Yang, J.; Rérat, A.; Lim, Y. J.; Gosmini, C.; Yoshikai, N. Cobalt-Catalyzed Enantio4

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and Diastereoselective Hydroacylation of Trisubstituted Alkenes. Angew. Chem. Int.
Ed. 2017, 56, 2449-2453.
Wu, J.; Xu, K.; Hirao, H.; Yoshikai, N. Pd-Catalyzed, Ligand-Enabled Stereoselective
1,2-Iodine(III) Shift/1,1-Carboxyalkynylation of Alkynylbenziodoxoles. Chem. Eur.
J. 2017, 23, 1521-1525.
Xu, W.; Yoshikai, N. N–H Imine as a Powerful Directing Group for Cobalt-Catalyzed
Olefin Hydroarylation. Angew. Chem. Int. Ed. 2016, 55, 12731-12735.
Xu, W.; Pek, J. H.; Yoshikai, N. Cobalt-Catalyzed, Imine-Directed Olefin
Hydroarylation under Grignard-Free Conditions. Adv. Synth. Catal. 2016, 358, 25642568
Wu, J.; Deng, X.; Hirao, H.; Yoshikai, N. Pd-Catalyzed Conversion of Alkynyl-λ3iodanes to Alkenyl-λ3-iodanes via Stereoselective 1,2-Iodine(III) Shift/1,1Hydrocarboxylation. J. Am. Chem. Soc. 2016, 138, 9105-9108.
Tan, W. W.; Yoshikai, N. Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes andDiazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, andThiophenes. J. Org. Chem. 2016, 81, 5566-5573.
Yan, J.; Yoshikai, N. Cobalt-Catalyzed Arylative Cyclization of Acetylenic Esters and
Ketones with Arylzinc Reagents through 1,4-Cobalt Migration. ACS Catal. 2016, 6,
3738-3742.
Wu, B.; Yoshikai, N. Recent Developments in Synthetic Methods for
Benzo[b]heteroles. Org. Biomol. Chem. 2016, 14, 5402-5416.
Yang, J.; Yoshikai, N. Cobalt-Catalyzed Annylation of Salicylaldehydes and Alkynes
to Form Chromones and 4-Chromanones. Angew. Chem. Int. Ed. 2016, 55, 28702874.
Wu, J.; Yoshikai, N. Cobalt-Catalyzed Alkenylzincation of Unfunctionalized Alkynes.
Angew. Chem. Int. Ed. 2016, 55, 336-340.
Wu, B.; Chopra, R.; Yoshikai, N. One-Pot Benzo[b]phosphole Synthesis throughSequential Alkyne Arylmagnesiation, Electrophilic Trapping, and Intramolecular
Phospha-Friedel–Crafts Cyclization. Org. Lett. 2015, 17, 5666-5669.
Wu, J.; Yoshikai, N. Modular Synthesis of Multisubstituted Furans throughPalladium-Catalyzed Three-Component Condensation of Alkynylbenziodoxoles,
Carboxylic Acids, and Imines. Angew. Chem. Int. Ed. 2015, 54, 11107-11111.
Xu, W.; Paira, R.; Yoshikai, N. Ortho-C–H Benzylation of Aryl Imines with Benzyl
Phosphates under Cobalt–Pyphos Catalysis. Org. Lett. 2015, 17, 4192-4195.
Tan, W. W.; Yoshikai, N. Copper-Catalyzed Condensation of Imines and α-Diazo-βdicarbonyl Compounds: Modular and Regiocontrolled Synthesis of Multisubstituted
Pyrroles. Chem. Sci. 2015, 6, 6448-6455.
Wu, B.; Yoshikai, N. Conversion of 2-Iodobiaryls into 2,2-Diiodobiaryls via OxidationIodination Sequences: A Versatile Route to Ladder-Type Heterofluorenes. Angew.
Chem. Int. Ed. 2015, 54, 8736-8739.
Yang, J.; Seto, Y. W.; Yoshikai, N. Cobalt-Catalyzed Intermolecular Hydroacylationof Olefins through Chelation-Assisted Imidoyl C–H Activation. ACS Catal. 2015, 5,3054-3057.
Yoshikai, N. Cp*CoIII-Catalyzed C–H Activation of (Hetero)arenes: Expanding the
Scope of Base-Metal-Catalyzed C–H Functionalization. ChemCatChem 2015, 7,
732-734. (one of most accessed articles in Feb 2015)
Wong, M. Y.; Yamakawa, T.; Yoshikai, N. Iron-Catalyzed Directed C2-Alkylation and
Alkenylation of Indole with Vinylarenes and Alkynes. Org. Lett. 2015, 17, 442-445.
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Lee, P.-S.; Yoshikai, N. Cobalt-Catalyzed Enantioselective Directed C–H Alkylationof Indoles with Styrenes. Org. Lett. 2015, 17, 22-25.
Yamakawa, T.; Seto, Y. W.; Yoshikai, N. Cobalt-Catalyzed Directed Alkylation of
Olefinic C–H Bond with Primary and Secondary Alkyl Chlorides. Synlett 2015, 26,
340-344.
Xu, W.; Yoshikai, N. Highly Linear-Selective Cobalt-Catalyzed Addition of Aryl
Imines to Styrenes: Reversing Intrinsic Regioselectivity by Ligand Elaboration.
Angew. Chem. Int. Ed. 2014, 53, 14166-14170.
Yang, J.; Yoshikai, N. Cobalt-Catalyzed Enantioselective Intramolecular
Hydroacylation of Ketones and Olefins. J. Am. Chem. Soc. 2014, 136, 16748-16751.
[one of most accessed articles in Nov 2014]
Yoshikai, N. Cobalt-Catalyzed C–C Bond-Forming Reactions via Chelation-Assisted
C–H Activation. J. Synth. Org. Chem. Jpn. 2014, 72, 1198-1206.
Tan, W. W.; Hou, X.; Yoshikai, N. Pd(II)/Bu4NBr/DMSO Catalytic System for
Practical Synthesis of Indoles and Pyrroles from Imines through Aerobic
Dehydrogenative Cyclization. Synthesis 2014, 46, 2727-2733.
Lu, B.; Wu, J.; Yoshikai, N. Palladium-Catalyzed Condensation of N-Aryl Imines andAlkynylbenziodoxolones To Form Multisubstituted Furans. J. Am. Chem. Soc. 2014,
136, 11598-11601.
Yoshikai, N. Development of Cobalt-Catalyzed C–H Bond Functionalization
Reactions. Bull. Chem. Soc. Jpn. 2014, 87, 843-857.
Karthikeyan, J.; Yoshikai, N. Rhodium(III)-Catalyzed Directed peri-C–H Alkenylationof Anthracene Derivatives. Org. Lett. 2014, 16, 4224-4227.
Gao, K.; Yamakawa, T.; Yoshikai, N. Cobalt-Catalyzed Chelation-Assisted Alkylationof Arenes with Primary and Secondary Alkyl Halides. Synthesis 2014, 46, 2024-2039(Feature Article).
Wu, B.; Santra, M.; Yoshikai, N. A Highly Modular One-Pot Multicomponent
Approach to Functionalized Benzo[b]phosphole Derivative, Angew. Chem. Int. Ed.
2014, 53, 7543-7546. [Highlighted in Synfacts 2014, 10, 928]
Tan, B.-H.; Yoshikai, N. Cobalt-Catalyzed Addition of Arylzinc Reagents to
Norbornene Derivatives through 1,4-Cobalt Migration. Org. Lett. 2014, 16, 33923395.
Asako, S.; Norinder, J.; Ilies, L.; Yoshikai, N.; Nakamura, E. ortho-Allylation of 1Arylpyrazole with Allyl Phenyl Ether via Iron-Catalyzed C–H Bond Activation under
Mild Conditions. Adv. Synth. Catal. 2014, 356, 1481-1485.
Gao, K.; Paira, R.; Yoshikai, N. Cobalt-Catalyzed Ortho-C–H Alkylation of 2Arylpyridines via Ring-Opening of Aziridines. Adv. Synth. Catal. 2014, 356, 14861490.
Yoshikai, N.; Gao, K. Cobalt-Catalyzed Directed Alkylation of Arenes with Primaryand Secondary Alkyl Halides. Pure Appl. Chem. 2014, 86, 419-424.
Yamakawa, T.; Yoshikai, N. Alkene Isomerization–Hydroarylation Tandem Catalysis:
Indole C2-Alkylation with Aryl-Substituted Alkenes Leading to 1,1-Diarylalkanes.
Chem. Asian J. 2014, 9, 1242-1246.
Gao, K.; Yoshikai, N. Low-Valent Cobalt Catalysis: New Opportunities for C–H
Functionalization. Acc. Chem. Res. 2014, 47, 1208-1219.
Rijs, N. J.; Yoshikai, N.; Nakamura, E.; O'Hair, R. A. J. Unraveling Organocuprate
Complexity: Fundamental Insights into Intrinsic Group Transfer Selectivity in
Alkylation Reactions. J. Org. Chem. 2014, 79, 1320-1334.
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Harano, K.; Takenaga, S.; Okada, S.; Niimi, Y.; Yoshikai, N.; Isobe, H.; Suenaga, K.;
Kataura, H.; Koshino, M.; Nakamura, E. Conformational Analysis of Single
Perfluoroalkyl Chains by Single-Molecule Real-Time Transmission Electron
Microscopic Imaging. J. Am. Chem. Soc. 2014, 136, 466-473.
Wu, B.; Yoshikai, N. Versatile Synthesis of Benzothiophenes andBenzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, andElemental Chalcogens. Angew. Chem. Int. Ed. 2013, 52, 10496-10499.
Deb, I.; Yoshikai, N. Phenanthridine Synthesis through Iron-Catalyzed
Intramolecular N-Arylation of O-acetyl Oxime, Org. Lett. 2013, 15, 4254-4257.
Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Intramolecular Olefin Hydroarylation Leading
to Dihydropyrroloindoles and Tetrahydropyridoindoles. Angew. Chem. Int. Ed. 2013,
52, 8574-8578.
Dong, J.; Lee, P.-S.; Yoshikai, N. Cobalt-Catalyzed Branched-Selective Addition of
Aromatic Ketimines to Styrenes under Room Temperature Conditions. Chem. Lett.
2013, 42, 1140-1142.
Gao, K.; Yoshikai, N. Cobalt-Catalyzed Ortho Alkylation of Aromatic Imines withPrimary and Secondary Alkyl Halides. J. Am. Chem. Soc. 2013, 135, 9279-9282.
Chen, Z.; Lu, B.; Ding, Z.; Gao, K.; Yoshikai, N. α-Palladation of Imines as Entry to
Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of N-Allylimines to
Pyrroles. Org. Lett. 2013, 15, 1966-1969.
Yoshikai, N.; Wei, Y. Synthesis of Pyrroles, Indoles, and Carbazoles throughTransition Metal-Catalyzed C–H Functionalization. Asian J. Org. Chem. 2013, 2,
466-478.
Yamakawa, T.; Yoshikai, N. Cobalt-Catalyzed ortho-Alkenylation of Aromatic
Aldimines via Chelation-Assisted C–H Bond
Activation.
Tetrahedron2013,
69, 4459-4465.
Wei, Y.; Yoshikai, N. Modular Pyridine Synthesis from Oximes and Enals through
Synergistic Copper/Iminium Catalysis. J. Am. Chem. Soc. 2013, 135, 3756-3759.
Yamakawa, T.; Yoshikai, N. Annulation of α,β-Unsaturated Imines and Alkynes via
Cobalt-Catalyzed Olefinic C–H Activation. Org. Lett. 2013, 15, 196-199.
Lee, P.-S.; Yoshikai, N. Aldimine-Directed Branched-Selective Hydroarylation of
Styrenes. Angew. Chem. Int. Ed. 2013, 52, 1240-1244.
Hajra, A.; Wei, Y.; Yoshikai, N. Palladium-Catalyzed Aerobic Dehydrogenative
Aromatization of Cyclohexanone Imines to Arylamines. Org. Lett. 2012, 14, 54885491.
Ilies, L.; Matsumoto, A.; Kobayashi, M.; Yoshikai, N.; Nakamura, E. Synthesis of
Polysubstituted Naphthalenes by Iron-Catalyzed [2+2+2] Annulation of Grignard
Reagents with Alkynes. Synlett 2012, 2381-2384.
Tan, B.-H.; Dong, J.; Yoshikai, N. Cobalt-Catalyzed Addition of Arylzinc Reagents to
Alkynes to Form ortho-Alkenylarylzinc Species through 1,4-Cobalt Migration. Angew.
Chem. Int. Ed. 2012, 51, 9610-9614.
Ding, Z.; Yoshikai, N. C2-Alkylation of N-Pyrimidylindole with Vinylsilanes via CobaltCatalyzed C-H Bond Activation. Beilstein J. Org. Chem. 2012, 8, 1536-1542.
Gao, K.; Lee, P.-S.; Long, C.; Yoshikai, N. Cobalt-Catalyzed Ortho-Arylation of
Aromatic Imines with Aryl Chlorides. Org. Lett. 2012, 14, 4234-4237.
Nakamura, Y.; Yoshikai, N.; Ilies, L.; Nakamura, E. Nickel-Catalyzed
Monosubsitution of Polyfluoroarenes with Organozinc Reagents Using
Alkoxydiphosphine Ligand. Org. Lett. 2012, 14, 3316-3319.
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Adak, L.; Yoshikai, N. Iron-Catalyzed Annulation Reaction of Arylindium Reagentsand Alkynes to Produce Substituted Naphthalenes. Tetrahedron 2012, 68, 51675171.
Wei, Y.; Deb, I.; Yoshikai, N. Palladium-Catalyzed Aerobic Oxidative Cyclization of
N-Aryl Imines: Indole Synthesis from Anilines and Ketones. J. Am. Chem. Soc.
2012, 134, 9098-9101.
Ding, Z.; Yoshikai, N. Mild and Efficient C2-Alkenylation of Indoles with Alkynes
Catalyzed by a Cobalt Complex. Angew. Chem. Int. Ed. 2012, 4698-4701.
Gao, K.; Yoshikai, N. Cobalt-Catalyzed Arylation of Aldimines via Directed C–H
Bond Functionalization: Addition of 2-Arylpyridines and Self-Coupling of Aromatic
Aldimines. Chem. Commun. 2012, 48, 4305-4307.
Yoshikai, N.; Nakamura, E. Mechanisms of Nucleophilic Organocopper(I) Reactions.
Chem. Rev. 2012, 112, 2339-2372.
Ilies, L.; Kobayashi, M.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. Iron-Catalyzed
Nitrogen-Directed Coupling of Arene and Aryl Bromides Mediated by Metallic
Magnesium. Adv. Synth. Catal. 2012, 354, 593-596.
Rijs, N.; Yoshikai, N.; Nakamura, E.; O'Hair, R. A. J. Gas-Phase Reactivity of Group
11 Dimethylmetallates with Allyl Iodide. J. Am. Chem. Soc. 2012, 134, 2569-2580.
Yoshikai, N.; Asako, S.; Yamakawa, T.; Ilies, L.; Nakamura, E. Iron-Catalyzed C–H
Bond Activation for the ortho-Arylation of Aryl Pyridines and Imines with Grignard
Reagents. Chem. Asian. J. 2011, 6, 3059-3065.
Lee, P.-S.; Fujita, T.; Yoshikai, N. Cobalt-Catalyzed, Room-Temperature Addition of
Aromatic Imines to Alkynes via Directed C–H Bond Activation. J. Am. Chem. Soc.
2011, 133, 17283-17295.
Wei, Y.; Yoshikai, N. Oxidative Cyclization of 2-Arylphenols to Dibenzofurans under
Pd(II)/Peroxybenzoate Catalysis. Org. Lett. 2011, 13, 5504-5507.
Adak, L.; Yoshikai, N. Cobalt-Catalyzed Preparation of Arylindium Reagents fromAryl and Heteroaryl Bromides. J. Org. Chem. 2011, 76, 7563-7568.
Gao, K.; Yoshikai, N. Cobalt–Phenanthroline Catalysts for the ortho Alkylation of
Aromatic Imines under Mild Conditions. Angew. Chem. Int. Ed. 2011, 50, 6888-6892.
Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Alkenylation of Thiazoles with Alkynes via
C–H Bond Functionalization. Synthesis 2011, 2561-2566.
Chen, Q.; Ilies, L.; Yoshikai, N.; Nakamura, E. Cobalt-Catalyzed Coupling of Alkyl
Grignard Reagent with Benzamide and 2-Phenylpyridine Derivatives throughDirected C–H Bond Activation under Air. Org. Lett. 2011, 13, 3232-3234.
Yoshikai,N.
Cobalt-Catalyzed,
Chelation-Assisted
C-H
Bond
Functionalization. Synlett 2011, 1047-1051. * Invited highlight article
Jin, M.-Y.; Yoshikai, N. Cobalt–Xantphos Catalyzed, LiCl-Mediated Preparation of
Arylzinc Reagents from Aryl Iodides, Bromides, and Chlorides. J. Org. Chem. 2011,76, 1972-1978 (Featured Article).
Gao, K.; Yoshikai, N. Regioselectivity-Switchable Hydroarylation of Styrenes. J. Am.
Chem. Soc. 2011, 133, 400-402.
Adak, L.; Chan, W. C.; Yoshikai, N. Nickel-Catalyzed, Directing Group-Assisted [2 +2 + 2] Cycloaddition of Imine and Alkynes. Chem. Asian. J. 2011, 6, 359-362.
Ding, Z.; Yoshikai, N. Cobalt-Catalyzed Addition of Azoles to Alkynes. Org. Lett.
2010, 12, 4180-4183.
Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. Cobalt-Catalyzed Hydroarylation of
Alkynes through Chelation-Assisted C-H Bond Activation. J. Am. Chem. Soc. 2010,
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Nakamura, E.; Yoshikai, N. Low-Valent Iron-Catalyzed C–C Bond Formation—
Addition, Substitution, and C–H Bond Activation. J. Org. Chem. 2010, 75, 6061-6067.
Ilies, L.; Okabe, J.; Yoshikai, N.; Nakamura, E. Iron-Catalyzed, Directed Oxidative
Arylation of Olefins with Organozinc and Grignard Reagents. Org. Lett. 2010, 12,2838-2840.
Gärtner, T.; Yoshikai, N.; Neumeier, M.; Nakamura, E.; Gschwind, R. M. Ligand
Exchange Reactions in Cu(III) Complexes: Mechanistic Insights by Combined NMR
and DFT Studies. Chem. Commun. 2010, 46, 4625-4626.
Yoshikai, N.; Mieczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. Iron-Catalyzed
C-C Bond Formation at α-Position of Aliphatic Amines via C-H Bond Activation
through 1,5-Hydrogen Transfer. J. Am. Chem. Soc. 2010, 132, 5568-5569.
Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Iron-Catalyzed Direct
Arylation of Aryl Pyridines and Imines Using Oxygen as an Oxidant. Synlett 2010,313-316.
Yoshikai, N.; Matsuda, H.; Nakamura, E. Hydroxyphosphine Ligand for NickelCatalyzed Cross-Coupling through Nickel/Magnesium Bimetallic Cooperation. J. Am.
Chem. Soc. 2009, 131, 9590-9599.
Yoshikai, N.; Miura, K.; Nakamura, E. Enantioselective Copper-Catalyzed Allylic
Substitution with Aminohydroxyphosphine Ligand. Adv. Synth. Catal. 2009, 351,
1014-1018.
Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Iron-Catalyzed
Chemoselective ortho Arylation of Aryl Imines by Directed C-H Bond Activation.
Angew. Chem. Int. Ed. 2009, 48, 2925-2928.
Yoshikai, N.; Zhang, S.-L.; Yamagata, K.-i.; Tsuji, H.; Nakamura, E. Mechanistic
Study of the Manganese-Catalyzed [2 + 2 + 2] Annulation of 1,3-DicarbonylCompounds and Terminal Alkynes. J. Am. Chem. Soc. 2009, 131, 4099-4109.
Yoshikai, N.; Matsuda, H.; Nakamura, E. Ligand Exchange as the First Irreversible
Step in the Nickel-Catalyzed Cross-Coupling Reaction of Grignard Reagents. J. Am.
Chem. Soc. 2008, 130, 15258-15259.
Yoshikai, N.; Zhang, S.-L.; Nakamura, E. Origin of the Regio- and Stereoselectivityof Allylic Substitution of Organocopper Reagents. J. Am. Chem. Soc. 2008, 130,12862-12863.
Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. Iron-Catalyzed Direct
Arylation through Directed C-H Bond Activation. J. Am. Chem. Soc. 2008, 130, 58585859.
Yoshikai, N.; Iida, R.; Nakamura, E. Mechanism of Nucleophilic Substitution of Acyl
Electrophiles using Lithium Organocuprates. Adv. Synth. Catal. 2008, 350, 10631072.
Hajra, A.; Yoshikai, N.; Nakamura, E. Aminohydroxyphosphine Ligands for CopperCatalyzed Enantioselective Conjugate Addition of Organozinc Reagents. Org. Lett.
2006, 8, 4153-4155.
Yoshikai, N.; Yamanaka, M.; Ojima, I.; Morokuma, K.; Nakamura, E. Bimetallic
Synergism in Alkyne Silylformylation Catalyzed by Cobalt-Rhodium Mixed-Metal
Cluster. Organometallics 2006, 25, 3867-3875.
Yoshikai, N.; Yamashita, T.; Nakamura, E. Mechanism of Remote Conjugate
Addition of a Lithium Organocuprate to Polyconjugated Carbonyl Compounds. Chem.
Asian. J. 2006, 1, 322-330.
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Norinder, J.; Bäckvall, J.-E.; Yoshikai, N.; Nakamura, E. Unusual Homo-Coupling in
the Reaction of Diorganocuprates with an Allylic Halide. Organometallics 2006, 25,
2129-2132.
Yoshikai, N.; Mashima, H.; Nakamura, E. Nickel-Catalyzed Cross-Coupling Reactionof Aryl Fluorides and Chlorides with Grignard Reagents under Nickel/Magnesium
Bimetallic Cooperation. J. Am. Chem. Soc. 2005, 127, 17978-17979.
Yoshikai, N.; Yamashita, T.; Nakamura, E. Mechanism of Remote Conjugate
Addition of a Lithium Organocuprate to a Polyconjugated Carbonyl Compound.
Angew. Chem. Int. Ed. 2005, 44, 4721-4723.
Ammal, S. C.; Yoshikai, N.; Inada, Y.; Nishibayashi, Y.; Nakamura, E. Synergistic
Dimetallic Effects in Propargylic Substitution Reaction Catalyzed by Thiolate-Bridged
Diruthenium Complex. J. Am. Chem. Soc. 2005, 127, 9428-9438.
Kinoshita, N.; Marx, K. H.; Tanaka, K.; Tsubaki, K.; Kawabata, T.; Yoshikai, N.;
Nakamura, E. Enantioselective Allylic Substitution of Cinnamyl Esters Catalyzed by
Iridium-Chiral Aryl Phosphite Complex: Conspicuous Change in the Mechanistic
Spectrum by a Counter Cation and Solvent. J. Org. Chem. 2004, 69, 7960-7964.
Yoshikai, N.; Ammal, S. C.; Nakamura, E. L-shaped Three-center Two-electron (CC-C)+ Bonding Array. J. Am. Chem. Soc. 2004, 126, 12941-12948.
Yoshikai, N.; Nakamura, E. Mechanism of Substitution Reaction on sp2-Carbon
Center with Lithium Organocuprate. J. Am. Chem. Soc. 2004, 126, 12264-12265.
Nakamura, E.; Yoshikai, N. On the Mechanism of Higher-Order Cuprate, Alias
Lipshutz Cuprate. Bull. Chem. Soc. Jpn. 2004, 77, 1-12.
Yoshikai, N.; Nakamura, E. Theoretical Studies on Diastereo- and Enantioselective
Rhodium-Catalyzed Cyclization of Diazo Compound via Intramolecular C-H Bond
Insertion. Adv. Synth. Catal. 2003, 345, 1159-1171.
Nakamura, E.; Yoshikai, N.; Yamanaka, M. Mechanism of C-H Bond Activation/C-C
Bond Formation Reaction between Diazo Compound and Alkane Catalyzed by
Dirhodium Tetracarboxylate. J. Am. Chem. Soc. 2002, 124, 7181-7192.
Nakamura, M.; Yoshikai, N.; Nakamura, E. Carbozincation of Dipolar
Trimethylenemethane. A New Route to Functionalized Organozinc Reagents. Chem.
Lett. 2002, 146-147.
Nakamura, M.; Yoshikai, N.; Toganoh, M.; Nakamura, E. [3 + 3] Cycloaddition of
Dipolar Trimethylenemethane with Active Methylene Compound. Synlett 2001, 10301033.
Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Kinetic Reactivity of Higher
Order Cuprate in SN2 Alkylation Reaction. Angew. Chem. Int. Ed. 2001, 40, 19351938.

Book Chapters11.
Science of Synthesis Base-Metal Catalysis, Vol. 2, Yoshikai, N. Ed.; Thieme; Stuttgart,
2023.
10.
Science of Synthesis Base-Metal Catalysis, Vol. 1, Yoshikai, N. Ed.; Thieme; Stuttgart,
2022.
9.
Organocobalt Complexes in C–H Activation, Yoshikai, N. In Comprehensive
Organometallic Chemistry IV, Mayer, K.; O’Hare, D.; Parkin, G. Eds., Elsevier, 2022.
8.
Cobalt-Catalyzed Asymmetric C–H Functionalization, Yoshikai, N. In Handbook of
C–H Functionalization, Maiti, D. Ed., Wiley, 2022.
7.
Cobalt-Catalyzed C–H Activation, Yoshikai, N. In Chemistry of Organocobalt
10

6.
5.
4.

3.

2.
1.

Compounds, Gosmini, C.; Marek, I. Eds., Wiley, 2022.
Benzo[b]thiophenes, Yoshikai, N.; Rayner, C. M.; Graham, M. A. In Science ofSynthesis Knowledge Updates, (2020) 2, 53 (DOI: 10.1055/sos-SD-110-01749).
Cobalt-Catalysed C–H Functionalization, Yoshikai, N. In Cobalt Catalysis in Organic
Synthesis: Methods and Reactions, Hapke, M.; Hilt, G. Eds., Wiley, 2020.
Hydroarylation of Alkynes and Alkenes using Group 7–9 First Row Transition Metal
Catalysts, Yoshikai, N. In Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds,
Ackermann, L.; Gunnoe, T. B.; Habgood, L. G. Eds., Wiley, 2018.
Heterocycle Synthesis via Co-Catalyzed C–H Activation/Functionalization, Yoshikai,
N. In Transition Metal-Catalyzed Heterocycle Synthesis via C–H Activation, Wu, X.-F.
Ed., Wiley, 2016.
Iron-Catalyzed C–C Bond Formation with C–H Bond Activation, Yoshikai, N. In
Chemistry of Organoiron Compounds, Rappoport, Z.; Marek, I. Eds., Wiley, 2014.
Theory of Organocopper-Mediated Reactions, Nakamura, E.; Yoshikai, N. In
Chemistry of Organocopper Compounds, Rappoport, Z.; Marek, I. Eds., Wiley, 2009.

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