Photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement

被引：50
作者：
He, Fu-Sheng [1 ,2 ]
Wu, Youqian [1 ,2 ]
Li, Xiaofang [3 ]
Xia, Hongguang [1 ,2 ]
Wu, Jie [4 ,5 ]
机构：
[1] Zhejiang Univ, Sch Med, Affiliated Hosp 1, Dept Biochem, Hangzhou 310058, Zhejiang, Peoples R China
[2] Zhejiang Univ, Sch Med, Affiliated Hosp 1, Res Ctr Clin Pharm, Hangzhou 310058, Zhejiang, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China
[4] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China
[5] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 11期
基金：
国家重点研发计划; 中国国家自然科学基金;
关键词：
QUINOLINE N-OXIDES; DIRECT BETA-ARYLATION; C-H BONDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT REACTION; DIARYLIODONIUM SALTS; SELECTIVE SYNTHESIS; COUPLING REACTIONS; TERMINAL ALKYNES;
D O I：
10.1039/c9qo00300b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A photoredox-catalyzed sulfonylation of alkenylcyclobutanols with the insertion of sulfur dioxide through semipinacol rearrangement under visible light irradiation is developed. This protocol provides an efficient and facile route to beta-sulfonated ketones bearing a-carbon quaternary centers under mild conditions, which features good functional group compatibility. Preliminary mechanistic investigation shows that an arylsulfonyl radical-induced 1,2-carbon migration process is involved.
引用
收藏
页码：1873 / 1878
页数：6
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