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. 2020 Dec 7;59(50):22441-22445.
doi: 10.1002/anie.202010509. Epub 2020 Oct 7.

Copper-Catalyzed Carbonylative Hydroamidation of Styrenes to Branched Amides

Yang Yuan  1 , Fu-Peng Wu  1 , Claas Schünemann  1 , Jens Holz  1 , Paul C J Kamer  1 , Xiao-Feng Wu  1   2
Affiliations

Copper-Catalyzed Carbonylative Hydroamidation of Styrenes to Branched Amides

Yang Yuan et al. Angew Chem Int Ed Engl. .

Abstract

Amides are one of the most ubiquitous functional groups in synthetic and medicinal chemistry. Novel and rapid synthesis of amides remains in high demand. In this communication, a general and efficient procedure for branch-selective hydroamidation of vinylarenes with hydroxyamine derivatives enabled by copper catalysis has been developed for the first time. The reaction proceeds under mild conditions and tolerates a broad range of functional groups. Applying a chiral phosphine ligand, an enantioselective variant of this transformation was achieved, affording a variety of chiral α-amides with excellent enantioselectivities (up to 99 % ee) and high yields.

Keywords: amides; carbonylation; copper; enantioselectivity; hydroamidation.

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