Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions

被引:128
作者
Cai, Shunyou [1 ,2 ]
Xu, Yaohui [1 ]
Chen, Danling [1 ]
Li, Lihuang [1 ]
Chen, Qifa [1 ]
Huang, Mingqiang [1 ]
Weng, Wen [1 ]
机构
[1] Minnan Normal Univ, Sch Chem & Environm, Key Lab Modern Analyt Sci & Separat Technol Fujia, Zhangzhou 363000, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Key Lab Chem Genom, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
IODINE-MEDIATED SYNTHESIS; H BOND FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; VINYL SULFONES; EOSIN Y; CARBOXYLIC-ACIDS; C-C; (E)-VINYL SULFONES; COUPLING REACTIONS; ARYL SULFIDES;
D O I
10.1021/acs.orglett.6b01353
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylative cross-coupling reactions of cinnamic acids with sulfonylhydrazides were explored using oxygen as the sole terminal oxidant, realizing a conceptually novel technology for vinyl sulfone synthesis under the synergistic interactions of visible light irradiation, organic dye-type photocatalyst eosin Y, KI, and Cs2CO3 at room temperature.
引用
收藏
页码:2990 / 2993
页数:4
相关论文
共 69 条
[1]   Sulfones: new reagents in organocatalysis [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033
[2]   Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones [J].
Back, Thomas G. ;
Clary, Kristen N. ;
Gao, Detian .
CHEMICAL REVIEWS, 2010, 110 (08) :4498-4553
[3]   Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM ;
Bernini, R .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614
[4]   Visible-light-promoted syntheses of β-keto sulfones from alkynes and sulfonylhydrazides [J].
Cai, Shunyou ;
Chen, Danling ;
Xu, Yaohui ;
Weng, Wen ;
Li, Lihuang ;
Zhang, Ruijie ;
Huang, Mingqiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (18) :4205-4209
[5]   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
[6]   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
[7]   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
[8]   A nanocellulose dye conjugate for multi-format optical pH-sensing [J].
Chauhan, Prashant ;
Hadad, Caroline ;
Lopez, Ana Herreros ;
Silvestrini, Simone ;
La Parola, Valeria ;
Frison, Enrico ;
Maggini, Michele ;
Prato, Maurizio ;
Carofiglio, Tommaso .
CHEMICAL COMMUNICATIONS, 2014, 50 (67) :9493-9496
[9]   THE PREPARATION OF UNSATURATED SULFONES BY CONDENSATION REACTIONS [J].
CHODROFF, S ;
WHITMORE, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (03) :1073-1076
[10]   Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones [J].
Choi, Junwon ;
Martin-Gago, Pablo ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (34) :12161-12165