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An Iridium/Aluminum Cooperative Strategy for the β-C(sp )-H Borylation of Saturated Cyclic Amines. | LitMetric

An Iridium/Aluminum Cooperative Strategy for the β-C(sp )-H Borylation of Saturated Cyclic Amines.

Angew Chem Int Ed Engl

Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.

Published: June 2023

AI Article Synopsis

Article Abstract

Despite the widespread success in the functionalization of C(sp )-H bonds, the deliberate functionalization of C(sp )-H bonds in a highly site- and stereoselective manner remains a longstanding challenge. Herein, we report an iridium/aluminum cooperative catalytic system that enables the β-selective C-H borylation of saturated cyclic amines and lactams. Furthermore, we have accomplished an enantioselective variant using binaphthol-derived chiral aluminum catalysts to forge C-B bonds with high levels of stereocontrol. Computational studies suggest that the formation of a Lewis pair with the substrates is crucial to lower the energy of the transition state for the rate-determining reductive elimination step.

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Source
http://dx.doi.org/10.1002/anie.202300704DOI Listing

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