Copper(I)-Catalyzed Three-Component Selenosulfonation of Maleimides with Sulfonyl Hydrazides and Diselenides via Radical Relay

By employing Cu­(CH3CN)4PF6 as the catalyst and tert-butyl hydroperoxide as the oxidant, we realized a three-component radical selenosulfonation of substituted maleimides, sulfonyl hydrazides, and diphenyl diselenides, providing a series of 3,4-selenosulfonylated succinimides in moderate to good yie...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (22), p.15661-15669
Main Authors: Ruan, Hong-Li, Deng, Yun-Xia, Li, Zi-Jing, Zhao, Sheng-Yin
Format: Article
Language:English
Subjects:
Catalysis
Copper - chemistry
Hydrazines - chemistry
Iodine
Maleimides
Molecular Structure
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Summary:By employing Cu­(CH3CN)4PF6 as the catalyst and tert-butyl hydroperoxide as the oxidant, we realized a three-component radical selenosulfonation of substituted maleimides, sulfonyl hydrazides, and diphenyl diselenides, providing a series of 3,4-selenosulfonylated succinimides in moderate to good yields. This reaction features broad substrate scopes, high functional-group tolerability, and feasibility of gram-scale synthesis, enabling one-step construction of C–SO2 and C–Se bonds under mild reaction conditions. Preliminary mechanistic studies support the free-radical-induced pathway.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01907