Formation of the Tertiary Sulfonamide C(sp)-N Bond Using Alkyl Boronic Ester via Intramolecular and Intermolecular Copper-Catalyzed Oxidative Cross-Coupling.

J Org Chem

Department of Chemistry, College of National Science, Seoul National University, Gwanak-ro 1, Gwanak-gu, Seoul 08826, Republic of Korea.

Published: December 2021


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Article Abstract

A synthetic strategy for the formation of C(sp)-N bonds, particularly through a copper-catalyzed oxidative cross-coupling, is rare. Herein, we report a novel synthetic approach for the preparation of tertiary sulfonamides via copper-catalyzed intra- and intermolecular oxidative C(sp)-N cross-coupling reactions. This method allows the utilization of the readily available C(sp)-based pinacol boronate as a substrate and the tolerance of a wide range of functional groups under mild reaction conditions. The success of this strategy relies on the unprecedented additive effects of silanol and NaIO.

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http://dx.doi.org/10.1021/acs.joc.1c01759DOI Listing

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