化学
催化作用
镍
区域选择性
化学选择性
分子内力
磺酰
烷基
氧化加成
配体(生物化学)
组合化学
光催化
光化学
有机化学
立体化学
光催化
生物化学
受体
作者
Yu Zhou,Wenhui Yang,Nan‐Nan Dai,Jia-Yao Feng,Mingqi Yang,Wenqing Gao,Qiang Li,Chao Deng,Zhan Lu,Wen‐Ting Wei
出处
期刊:Organic Letters
[American Chemical Society]
日期:2024-06-10
卷期号:26 (24): 5074-5081
被引量:3
标识
DOI:10.1021/acs.orglett.4c01258
摘要
The nickel/photoredox dual catalysis system is an efficient conversion platform for the difunctionalization of unsaturated hydrocarbons. Herein, we disclose the first dual nickel/photoredox-catalyzed intramolecular 1,2-arylsulfonylation of allenes, which can accurately construct a C(sp2)–C(sp2) bond and a C(sp3)–S bond. The reaction exhibits excellent chemoselectivity and regioselectivity, allowing modular conformations of a diverse series of 3-sulfonylmethylbenzofuran derivatives. Control experiments showed that the bipyridine ligand is crucial for the formation of a stable σ-alkyl nickel intermediate, providing the possibility for sulfonyl radical insertion. Meanwhile, the electrophilic sulfonyl radical facilitates further oxidative addition of the σ-alkyl nickel intermediate and inhibits addition with allenes. In addition, control experiments, cyclic voltammetry tests, Stern–Volmer experiments, and density functional theory calculations afford evidence for the Ni(0)/Ni(I)/Ni(II)/Ni(III) pathway in this 1,2-arylsulfonylation.
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