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

J Org Chem. 2022 Nov 18;87(22):15661-15669. doi: 10.1021/acs.joc.2c01907. Epub 2022 Nov 1.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper* / chemistry
  • Hydrazines / chemistry
  • Iodine*
  • Maleimides
  • Molecular Structure

Substances

  • Copper
  • Maleimides
  • Hydrazines
  • Iodine