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Copper(I)-Catalyzed Three-Component Selenosulfonation of Maleimides with Sulfonyl Hydrazides and Diselenides via Radical Relay.
Ruan, Hong-Li; Deng, Yun-Xia; Li, Zi-Jing; Zhao, Sheng-Yin.
Affiliation
  • Ruan HL; College of Chemistry and Chemical Engineering, Donghua University, No. 2999 North Renmin Road, Shanghai, 201620, P. R. China.
  • Deng YX; College of Chemistry and Chemical Engineering, Donghua University, No. 2999 North Renmin Road, Shanghai, 201620, P. R. China.
  • Li ZJ; College of Chemistry and Chemical Engineering, Donghua University, No. 2999 North Renmin Road, Shanghai, 201620, P. R. China.
  • Zhao SY; College of Chemistry and Chemical Engineering, Donghua University, No. 2999 North Renmin Road, Shanghai, 201620, P. R. China.
J Org Chem ; 87(22): 15661-15669, 2022 11 18.
Article in En | MEDLINE | ID: mdl-36317696
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.
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Copper / Iodine Language: En Journal: J Org Chem Year: 2022 Document type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Copper / Iodine Language: En Journal: J Org Chem Year: 2022 Document type: Article