个人简介

Education: B.Sc., M.Sc., Ph.D., University of Tokyo

研究领域

Synthetic and Physical Organic Chemistry/Catalysis/Organometallic Chemistry

Research Interest Our major research interests focus on the development and mechanistic study of novel transition metal-catalyzed chemical transformations and their applications to the synthesis of interesting target molecules. Our research programs are primarily driven by our desire to uncover previously unknown chemical reactivities of elements and molecules by design, and to exploit such reactivities to develop highly efficient, mild, and selective organic reactions. Another important driving force is our interest in functional molecules, pi-conjugated molecules in particular. We develop our catalysts and reactions to allow us to access structurally and optoelectronically interesting compounds via unique and efficient routes. Some of our current research activities are summarized below. Catalytic C–H Bond Functionalization Transition metal-catalyzed functionalization reactions of C–H bonds have attracted much interest during the last decades as straightforward and economical alternatives to those relying on prefunctionalized substrates. While the majority of C–H functionalization catalysts have been based on noble second-row transition metals, first-row transition metals have not been extensively exploited regardless of their potential as cost-effective catalysts. Over the past few years, our group has pioneered cobalt catalysiss for C–H bond functionalization, and has been rapidly expanding its scope. We have thus far developed chelation-assisted and heteroatom-directed C–H alkenylation and alkylation reactions using alkynes and alkenes, where cobalt catalysts not only serve as mild and inexpensive alternatives to noble metal catalysts but also often exhibit unique reactivities and selectivities. Transition Metal Catalysis of Main Group Organometallics Regardless of the emergence of C–H functionalization, there exist some important molecular skeletons that are difficult to be accessed by this approach. To allow for the synthesis of such molecules, we have been developing new C–C bond forming reactions via transition metal catalysis of main group organometallics. Novel Synthetic Routes to Conjugated Systems We have been developing our catalytic reactions not only to explore novel chemical reactivities but also to aim at the synthesis of structurally and optoelectronically interesting molecules that could have potential applications as organic materials and catalyst architectures. Synthesis of such molecules based on our own and other synthetic methodologies are currently in progress.

近期论文

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Gao, K.; Paira, R.; Yoshikai, N. "Cobalt-Catalyzed Ortho-C–H Alkylation of 2-Arylpyridines via Ring-Opening of Aziridines", Adv. Synth. Catal. 2014, in press. Yoshikai, N.; Gao, K. "Cobalt-Catalyzed Directed Alkylation of Arenes with Primary and Secondary Alkyl Halides", Pure Appl. Chem. 2014, in press. 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, DOI: 10.1002/asia.201400135. Gao, K.; Yoshikai, N. "Low-Valent Cobalt Catalysis: New Opportunities for C–H Functionalization", Acc. Chem. Res. 2014, DOI: 10.1021/ar400270x. [One of most read 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. 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 and Benzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, and Elemental Chalcogens", Angew. Chem. Int. Ed. 2013, 52, 10496 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 with Primary 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 through Transition 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", Tetrahedron 2013, 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, 5488-5491. 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