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
[31]  
Jain P, 2017, NAT CHEM, V9, P140, DOI [10.1038/NCHEM.2619, 10.1038/nchem.2619]
[32]   Application of Fundamental Organometallic Chemistry to the Development of a Gold-Catalyzed Synthesis of Sulfinate Derivatives** [J].
Johnson, Miles W. ;
Bagley, Scott W. ;
Mankad, Neal P. ;
Bergman, Robert G. ;
Mascitti, Vincent ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (17) :4404-4407
[33]   FACTORS INFLUENCING POLYSULFONE FORMATION .2. A NEW METHOD OF INDUCTION WITH CONTROL OF POLYMER LENGTH [J].
KHARASCH, MS ;
FRIEDLANDER, HN .
JOURNAL OF ORGANIC CHEMISTRY, 1948, 13 (06) :882-885
[34]   Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction [J].
Li, Lu ;
Liu, Wenbo ;
Zeng, Huiying ;
Mu, Xiaoyue ;
Cosa, Gonzalo ;
Mi, Zetian ;
Li, Chao-Jun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8328-8331
[35]   Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source [J].
Li, Wanfang ;
Beller, Matthias ;
Wu, Xiao-Feng .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9513-9516
[36]   Palladium-Catalyzed Aminosulfonylation of Aryl Iodides by using Na2SO3 as the SO2 Source [J].
Li, Wanfang ;
Li, Haoquan ;
Langer, Peter ;
Beller, Matthias ;
Wu, Xiao-Feng .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) :3101-3103
[37]   Ruthenium-promoted reductive transformation of CO2 [J].
Li, Xuedong ;
He, Xing ;
Liu, Xiaofang ;
He, Liang-Nian .
SCIENCE CHINA-CHEMISTRY, 2017, 60 (07) :841-852
[38]   N-Radical Initiated Aminosulfonylation of Unactivated C(sp3)-H Bond through Insertion of Sulfur Dioxide [J].
Li, Yuewen ;
Mao, Runyu ;
Wu, Jie .
ORGANIC LETTERS, 2017, 19 (17) :4472-4475
[39]   A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO [J].
Li, Yuewen ;
Lu, Yiye ;
Mao, Runyu ;
Li, Zhiming ;
Wu, Jie .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09) :1745-1750
[40]   Direct vicinal difunctionalization of alkynes through trifluoromethylation and aminosulfonylation via insertion of sulfur dioxide under catalyst-free conditions [J].
Li, Yuewen ;
Xiang, Yuanchao ;
Li, Zhiming ;
Wu, Jie .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11) :1493-1497