Insertion of sulfur dioxide via a radical process: an efficient route to sulfonyl compounds

被引:322
作者
Qiu, Guanyinsheng [1 ]
Zhou, Kaida [2 ]
Gao, Liang [3 ]
Wu, Jie [2 ]
机构
[1] Jiaxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China
[2] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
[3] Ganzhou Teachers Coll, Dept Nat Sci & Comp Sci, Ganzhou 341000, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED AMINOSULFONYLATION; C-H FUNCTIONALIZATION; BETA-KETO SULFONES; 3-COMPONENT REACTION; ONE-POT; VICINAL DIFUNCTIONALIZATION; MULTICOMPONENT REACTION; C(SP(3))-H BOND; SULPHUR DIOXIDE; RECENT PROGRESS;
D O I
10.1039/c7qo01073g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review is focused on the recent advances in the chemistry of sulfur dioxide fixation through a radical process. Diverse sulfonyl compounds can be obtained efficiently under mild conditions. In general, aryl radicals, vinyl radicals, alkyl radicals, and nitrogen-centered radicals can react with sulfur dioxide, giving rise to sulfonyl radical intermediates. The resulting sulfonyl radicals can be captured by nucleophiles, olefins, and alkynes. The sources of aryl radicals from aryldiazonium salts, aryl halides, and diaryliodonium salts are demonstrated. It is believed that more amazing SO2-based achievements will be developed in the near future.
引用
收藏
页码:691 / 705
页数:15
相关论文
共 109 条
[61]  
Reed C. F., 1936, [No title captured], Patent No. [US 2046090A, 2046090A]
[62]   One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation [J].
Richards-Taylor, Charlotte S. ;
Blakemore, David C. ;
Willis, Michael C. .
CHEMICAL SCIENCE, 2014, 5 (01) :222-228
[63]   Synthesis of Sulfones from Organozinc Reagents, DABSO, and Alkyl Halides [J].
Rocke, Benjamin N. ;
Bahnck, Kevin B. ;
Herr, Michael ;
Lavergne, Sophie ;
Mascitti, Vincent ;
Perreault, Christian ;
Polivkova, Jana ;
Shavnya, Andrei .
ORGANIC LETTERS, 2014, 16 (01) :154-157
[64]   Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl propenones [J].
Shen, Zheng-Jia ;
Wu, Ya-Nan ;
He, Chun-Lan ;
He, Long ;
Hao, Wen-Juan ;
Wang, Ai-Fang ;
Tu, Shu-Jiang ;
Jiang, Bo .
CHEMICAL COMMUNICATIONS, 2018, 54 (05) :445-448
[65]   Reductive insertion of sulfur dioxide for the synthesis of trifluoromethyl thiolsulphonates through a one-pot reaction of aniline and trifluoromethanesulfanylamide [J].
Sheng, Jie ;
Li, Yuewen ;
Qiu, Guanyinsheng .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01) :95-100
[66]   DERIVATIVES OF CHLOROSULFONATED POLYETHYLENE AND THEIR INFRARED SPECTRA [J].
SMOOK, MA ;
PIESKI, ET ;
HAMMER, CF .
INDUSTRIAL AND ENGINEERING CHEMISTRY, 1953, 45 (12) :2731-2737
[67]  
Suarez E., 2001, Radicals in Organic Syntheses, P440
[68]  
Texter J., 2001, Reactions And Synthesis In Surfactant Systems
[69]   Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst [J].
Toutov, Anton A. ;
Liu, Wen-Bo ;
Betz, Kerry N. ;
Fedorov, Alexey ;
Stoltz, Brian M. ;
Grubbs, Robert H. .
NATURE, 2015, 518 (7537) :80-84
[70]   Structure of the products of the cyclooligomerization of sulfur dioxide with diethyl diallylmalonate [J].
Tsai, JY ;
Shevlin, PB .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3230-3234