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A copper-catalyzed insertion of sulfur dioxide via radical coupling

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Abstract

A copper-catalyzed three-component reaction of O-acyl oximes, DABCO·(SO2)2, and 2H-azirines under mild conditions has been achieved. This protocol provides an efficient route for the construction of various tetrasubstituted β-sulfonyl N-unprotected enamines in moderate to good yields with excellent stereoselectivity and regioselectivity. Notably, this method represents a rare example of 2H-azirines as useful synthons for β-functionalized N-unprotected enamines. Preliminary mechanistic studies indicate that the reaction proceeds through coupling of a sulfonyl radical and α-carbon radical via copper-catalyzed ring-opening C–C bond cleavage of O-acyl oxime and C–N bond cleavage of 2H-azirine with the insertion of sulfur dioxide.

Graphical abstract: A copper-catalyzed insertion of sulfur dioxide via radical coupling

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Article information


Submitted
15 Jan 2020
Accepted
13 Feb 2020
First published
13 Feb 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

A copper-catalyzed insertion of sulfur dioxide via radical coupling

J. Zhang, M. Yang, J. Liu, F. He and J. Wu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00375A

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