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Synlett 2019; 30(12): 1384-1400
DOI: 10.1055/s-0037-1611814
DOI: 10.1055/s-0037-1611814
account
Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources
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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Selected general reviews on C–H functionalization:
Reviews on Cp*RhIII-catalyzed C–H functionalization reactions:
General reviews on cobalt-catalyzed C–H functionalization:
Several stoichiometric C–H activation reactions with CoIII had been reported as of 2013:
Reviews on Cp*MIII-catalyzed C–H functionalization reactions:
Recent reviews on enantioselective C–H functionalization:
For external CMD, see:
For preparation and properties of Cp*CoIII-arene complexes:
For the isolation and structure of alkenyl-Co intermediates, see:
For other examples, see a review:
Early studies on Cp*CoIII-catalyzed C–H allylation reactions using activated allyl alcohols:
For early studies on Cp*CoIII-catalyzed C–H/C–F functionalization reactions:
Early studies on Cp*CoIII-catalyzed C–H amidation reactions using dioxazolones:
For dioxazolones as amidation reagents, see:
General reviews on enantioselective metal/organo hybrid catalysis:
For applications of ACDC to Pd-catalyzed C–H functionalization reactions, see:
A pioneering work:
Selected recent works:
For racemic reactions, see:
For related Pd-catalyzed enantioselective C–H functionalization reactions of thioamides, see:
For pioneering reports on Cp*CoIII-catalyzed racemic C(sp3)–H functionalization reactions, see: