Dual Copper/Photoredox Catalysis for Radical-Mediated Arylation and Alkylation of Sulfenamides

被引：1

作者：

Zhang, Mingjun ^{[1
]}

Tan, Yuhao ^{[1
]}

Yang, Hehe ^{[1
]}

Fu, Xiaoyang ^{[1
]}

Liu, Yuxiu ^{[1
]}

Wang, Ziwen ^{[1
,2
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, Res Inst Elemento Organ Chem, Coll Chem, Frontiers Sci Ctr New Organ Matter,State Key Lab E, Tianjin 300071, Peoples R China

[2] Tianjin Normal Univ, Coll Chem, Tianjin Key Lab Struct & Performance Funct Mol, Tianjin 300071, Peoples R China

来源：

ACS CATALYSIS | 2025年 / 15卷 / 05期

关键词：

sulfilimines; aryl radical-mediated XAT; arylsulfonium salts; alkyl iodides; photochemistry; HALOGEN; FUNCTIONALIZATION; SULFILIMINES; ACCESS;

D O I：

10.1021/acscatal.5c00082

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Radical-based pathways provide an attractive approach for constructing C(sp2/sp3)-S bonds from various substrates. Herein we report two strategies that can be used for aryl radical sulfilimination of aryl sulfonium salts and aryl radical-mediated cross-coupling reactions between alkyl iodides and sulfenamides, both via synergetic photoredox and copper catalysis. These mild, operationally simple reactions have a broad substrate scope and potential utility for late-stage functionalization of natural products and drug molecules. In addition, both sulfilimination reactions can be carried out on a gram scale under continuous-flow conditions. Mechanistic studies indicate that rapid abstraction of the iodine atom from the alkyl iodide by sterically hindered, electron-rich aryl radicals and tuning of the electronic properties of the copper catalyst by varying the ligand contribute to the chemoselectivity for alkylation.

引用

页码：4007 / 4016

页数：10

共 60 条

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