Visible-light-promoted syntheses of β-keto sulfones from alkynes and sulfonylhydrazides

被引：68
作者：
Cai, Shunyou [1 ,2 ]
Chen, Danling [1 ]
Xu, Yaohui [1 ]
Weng, Wen [1 ]
Li, Lihuang [1 ]
Zhang, Ruijie [1 ]
Huang, Mingqiang [1 ]
机构：
[1] Minnan Normal Univ, Fujian Prov Key Lab Modern Analyt Sci & Separat T, Sch Chem & Environm, Zhangzhou 363000, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, Key Lab Chem Genom, Sch Chem Biol & Biotechnol, Shenzhen 518055, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 18期
基金：
中国国家自然科学基金;
关键词：
PHOTOREDOX CATALYSIS; C-C; AEROBIC OXYSULFONYLATION; RADICAL ADDITIONS; VINYL SULFONES; DUAL-CATALYSIS; ALKENES; ACIDS; CYCLOADDITIONS; STRATEGY;
D O I：
10.1039/c6ob00617e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of functionalized beta-keto sulfones were smoothly prepared through oxysulfonylation of commercially available alkynes with sulfonylhydrazides under the synergistic interactions of visible light irradiation, Ru(bpy)(3)Cl-2 photocatalyst, oxygen, KI, and NaOAc basic additive under very mild reaction conditions.
引用
收藏
页码：4205 / 4209
页数：5
相关论文
共 74 条
[1]   Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ORGANIC LETTERS, 2011, 13 (09) :2406-2409
[2]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[3]   Photo-Organocatalysis of Atom-Transfer Radical Additions to Alkenes [J].
Arceo, Elena ;
Montroni, Elisa ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) :12064-12068
[4]   Structure-based design, synthesis, and biological evaluation of navel pyrrolyl aryl sulfones: HIV-1 non-nucleoside reverse transcriptase inhibitors active at nanomolar concentrations [J].
Artico, M ;
Silvestri, R ;
Pagnozzi, E ;
Bruno, B ;
Novellino, E ;
Greco, G ;
Massa, S ;
Ettorre, A ;
Loi, AG ;
Scintu, F ;
La Colla, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) :1886-1891
[5]   Gold Catalysis Coupled with Visible Light Stimulation: Syntheses of Functionalized Indoles [J].
Cai, Shunyou ;
Yang, Kai ;
Wang, David Zhigang .
ORGANIC LETTERS, 2014, 16 (10) :2606-2609
[6]   New Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis [J].
Cai, Shunyou ;
Zhang, Shaolong ;
Zhao, Yaohong ;
Wang, David Zhigang .
ORGANIC LETTERS, 2013, 15 (11) :2660-2663
[7]   Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals [J].
Cai, Shunyou ;
Zhao, Xinyang ;
Wang, Xinbo ;
Liu, Qisong ;
Li, Zigang ;
Wang, David Zhigang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8050-8053
[8]   Continuous Flow α-Trifluoromethylation of Ketones by Metal-Free Visible Light Photoredox Catalysis [J].
Cantillo, David ;
de Frutos, Oscar ;
Rincon, Juan A. ;
Mateos, Carlos ;
Kappe, C. Oliver .
ORGANIC LETTERS, 2014, 16 (03) :896-899
[9]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[10]   Rapid synthesis of sulfone derivatives as potential anti-infectious agents [J].
Curti, C. ;
Laget, M. ;
Carle, A. Ortiz ;
Gellis, A. ;
Vanelle, P. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (06) :880-884
12345678