Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer
Literature Information
Publication Date
2023-11-01
DOI
10.1039/D3QO01431B
Impact Factor
5.281
Authors
Li-Lin Jiang, Hui Qiu, Yu Zhou, Ling-Tao Wang, Wen-Hui Yang, Chao Deng, Wen-Ting Wei
View Original
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 CN 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.
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Organic Chemistry Frontiers
CiteScore:
7.8
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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