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
收藏
页码:2829 / 2839
页数:11
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