Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis

被引:51
作者
Arimori, Sadayuki [1 ]
Takada, Masahiro [1 ]
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
SILYL ENOL ETHERS; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; ENANTIOSELECTIVE FLUORINATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; TERMINAL ALKYNES; ARYL; REAGENT; SULFOXIDES; KETONES;
D O I
10.1039/c5dt02214b
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Trifluoromethylsulfinyl and trifluoromethylthio groups are both important substituents for pharmaceuticals, agrochemicals and functional materials. We herein report the trifluoromethylthiolation of allyl alcohols 2 with trifluoromethanesulfonyl hypervalent iodonium ylide 1 under copper catalysis to provide trifluoromethylsulfinyl compounds 3. Trifluoromethylthiolation of boronic acids 4 with 1 furnished trifluoromethylthio compounds 5.
引用
收藏
页码:19456 / 19459
页数:4
相关论文
共 63 条
[1]   Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides [J].
Adams, DJ ;
Goddard, A ;
Clark, JH ;
Macquarrie, DJ .
CHEMICAL COMMUNICATIONS, 2000, (11) :987-988
[2]   Catalytic Trifluoromethylation of Aryl- and Vinylboronic Acids by 2-Cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium Triflate [J].
Arimori, Sadayuki ;
Shibata, Norio .
ORGANIC LETTERS, 2015, 17 (07) :1632-1635
[3]   Trifluoromethylthiolation of Allylsilanes and Silyl Enol Ethers with Trifluoromethanesulfonyl Hypervalent Iodonium Ylide under Copper Catalysis [J].
Arimori, Sadayuki ;
Takada, Masahiro ;
Shibata, Norio .
ORGANIC LETTERS, 2015, 17 (05) :1063-1065
[4]   Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides [J].
Baert, Francois ;
Colomb, Julie ;
Billard, Thierry .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10382-10385
[5]   Fluorine in medicinal chemistry [J].
Böhm, HJ ;
Banner, D ;
Bendels, S ;
Kansy, M ;
Kuhn, B ;
Müller, K ;
Obst-Sander, U ;
Stahl, M .
CHEMBIOCHEM, 2004, 5 (05) :637-643
[6]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[7]   Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].
Chen, Chao ;
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457
[8]   Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur [J].
Chen, Chao ;
Xie, Yan ;
Chu, Lingling ;
Wang, Ruo-Wen ;
Zhang, Xingang ;
Qing, Feng-Ling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) :2492-2495
[9]   Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].
Chu, Lingling ;
Qing, Feng-Ling .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522
[10]   Beyond the Balz-Schiemann Reaction: The Utility of Tetrafluoroborates and Boron Trifluoride as Nucleophilic Fluoride Sources [J].
Cresswell, Alexander J. ;
Davies, Stephen G. ;
Roberts, Paul M. ;
Thomson, James E. .
CHEMICAL REVIEWS, 2015, 115 (02) :566-611