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Yoshikai, N. : 2023 Science of Synthesis, 2023/3: Base-Metal Catalysis 2 DOI: 10.1055/sos-SD-239-00042
Base-Metal Catalysis 2

2.6 C—H Functionalization Catalyzed by Low-Valent Cobalt

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Editor: Yoshikai, N. 

Authors: Adak, L. ; Aoki, S.; Banerjee, S. ; Bedford, R. B. ; Cheng, Z.; Costas, M. ; Gao, M.; Garai, B.; Ge, S. ; Gosmini, C. ; Hota, S. K.; Ilies, L. ; Jindal, A.; Kawanaka, Y.; Li, H. ; Li, M.; Liu, Q. ; Lu, Z. ; Mandal, R.; Matsunaga, S. ; Murarka, S. ; Nakamura, M. ; Nolla-Saltiel, R. ; Ollevier, T. ; Palone, A. ; Panda, S. P.; Sahoo, S.; Sang, J.; Schiltz, P.; Shenvi, R. A. ; Sundararaju, B. ; van der Puyl, V. ; Vicens, L. ; Wang, C. ; Wang, Y. ; Yang, X.; Yang, Y.; Yoshikai, N. ; Yoshino, T. ; Zeng, X. ; Zhang, G. 

Title: Base-Metal Catalysis 2

Print ISBN: 9783132455030; Online ISBN: 9783132455054; Book DOI: 10.1055/b000000440

1st edition © 2023 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

This review summarizes representative examples of catalytic C—H functionalization reactions mediated by low-valent cobalt complexes. Catalysts generated by the reduction of cobalt(II) or cobalt(III) precatalysts in the presence of appropriate supporting ligands have been demonstrated to promote a variety of alkylation, alkenylation, and arylation reactions of aromatic C(sp2)—H bonds, often with the assistance of directing groups. Well-defined cobalt(0) and cobalt(–I) complexes have also proved to catalyze some of these reactions. Low-valent cobalt complexes supported by bis(phosphinomethyl)pyridine, terpyridine, and diimine ligands have been identified as viable catalysts for the borylation of C(sp2)—H and C(sp3)—H bonds, where the cobalt catalysts exhibit unique site selectivity compared with well-established iridium catalysts. Other reactions such as 1,4-cobalt migration, hydroacylation, and C—H activation involving cobaltacyclopentene intermediates are also discussed.

Key words

base-metal catalysis - cobalt catalysis - C—H functionalization - C—H activation - C—H alkylation - C—H alkenylation - C—H arylation - C—H borylation - C—H carboxylation - hydroacylation - metal migration - directing groups
 
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