Visible-Light-Catalyzed C-C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3-Sulfonyl-1,2-dihydronaphthalenes

被引：47

作者：

Liu, Yu ^{[1
]}

Wang, Qiao-Lin ^{[1
]}

Chen, Zan ^{[1
]}

Zhou, Quan ^{[1
]}

Li, Hua ^{[1
]}

Zhou, Cong-Shan ^{[1
]}

Xiong, Bi-Quan ^{[1
]}

Zhang, Pan-Liang ^{[1
]}

Tang, Ke-Wen ^{[1
]}

机构：

[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 05期

基金：

中国国家自然科学基金;

关键词：

CARBONYL ALKYL BROMIDES; ARYL DIAZONIUM SALTS; METAL-FREE; VINYL SULFONES; FACILE ACCESS; N-OXIDES; CLEAVAGE; INSERTION; SULFUR; COPPER;

D O I：

10.1021/acs.joc.8b03261

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel visible-light-catalyzed sulfonylation/arylation of carbon-carbon sigma-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of C=C bond sulfonylation, C-C sigma-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C-C sigma-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C-C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C-S bond and a new C-C bond.

引用

页码：2829 / 2839

页数：11

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