Issue 24, 2023

Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer

Abstract

The trifunctionalization of alkenes has emerged as a versatile strategy for the efficient construction of diverse structural units and complex molecules in synthetic chemistry. Herein, we describe a novel 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters through simultaneous construction of four C–C bonds and a C[triple bond, length as m-dash]N bond in one pot based on the radical relay/1,5-hydrogen-atom transfer (HAT) processes under a mild copper catalytic system. The resulting reaction of spirocyclic derivatives displays high chemical selectivity, broad substrate scope, as well as high atom- and step-economy. Preliminary control experiments and density functional theory (DFT) calculations reveal sequential functionalizations and cyclizations in this transformation.

Graphical abstract: Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer

Supplementary files

Article information

Article type
Research Article
Submitted
05 Sept. 2023
Accepted
28 Okt. 2023
First published
01 Nov. 2023

Org. Chem. Front., 2023,10, 6096-6102

Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer

L. Jiang, H. Qiu, Y. Zhou, L. Wang, W. Yang, C. Deng and W. Wei, Org. Chem. Front., 2023, 10, 6096 DOI: 10.1039/D3QO01431B

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