Synlett 2019; 30(12): 1384-1400
DOI: 10.1055/s-0037-1611814
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© Georg Thieme Verlag Stuttgart · New York

Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Tatsuhiko Yoshino*
,
Shigeki Matsunaga*
This work was supported in part by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number JP15H05802) in Precisely Designed Catalysts with Customized Scaffolding and the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number JP18H04637) in Hybrid Catalysis.
Further Information

Publication History

Received: 06 March 2019

Accepted after revision: 10 April 2019

Publication Date:
07 May 2019 (online)


Abstract

This account describes Cp*CoIII-catalyzed C–H functionalization reactions developed in our group between 2013 and 2018. Cp*CoIII catalysts not only serve as inexpensive alternatives to Cp*RhIII catalysts but also exhibit unique reactivity and selectivity in several transformations. In the latter part of this review, we introduce catalytic asymmetric C–H functionalization reactions using achiral RhIII or CoIII catalysts with chiral disulfonates or carboxylic acids as external chiral sources.

1 Introduction and Overview

2 Cp*CoIII-Catalyzed C–H Functionalization Reactions

2.1 C–H Addition Reactions to Polar Double Bonds

2.2 Cp*Co(CO)I2 and [Cp*CoI2]2 Precursors for the C2-selective C–H Amidation of Indoles

2.3 C–H Functionalization of Carbamoyl-Protected Indoles Using Alkynes

2.4 C–H Allylation Using Allyl Alcohols

2.5 Cyclization Reactions of O-Acyloximes and Alkynes

2.6 Other Miscellaneous Reactions

3 Enantioselective C–H Functionalization Reactions by Hybrid Catalysis

3.1 Cp*RhIII/Chiral Disulfonate Catalysts for the Enantioselective C–H Addition to Enones

3.2 Enantioselective C–H Cleavage Using Chiral Carboxylic Acids

4 Summary and Perspective

 
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