Radical Difluororomethylation of Thiols with Difluoromethylphosphonium Triflate under Photoredox Catalysis

被引:34
作者
Ran, Yang [1 ]
Lin, Qing-Yu [1 ]
Xu, Xiu-Hua [1 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
基金
中国国家自然科学基金;
关键词
OXIDATIVE TRIFLUOROMETHYLTHIOLATION; S-DIFLUOROMETHYLATION; BORONIC ACIDS; DIFLUOROCARBENE; REAGENT; ARYL; ETHERS; DIFLUOROMETHYLTHIOETHERS; DISULFIDES; THIOETHERS;
D O I
10.1021/acs.joc.7b01041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient, visible light-induced radical difluoromethylation of aryl-, heteroaryl-, and alkylthiols with difluoromethyltriphenylphosphonium triflate was developed to afford various difluoromethyl thioethers in moderate to excellent yields. The key reaction features include the use of a readily available CF2H radical source, mild reaction conditions, and excellent chemoselective "thiol-difluoromethylation.
引用
收藏
页码:7373 / 7378
页数:6
相关论文
共 67 条
[1]   Perfluoroalkylation of aliphatic thiols in the presence of sodium hydroxymethanesulfinate [J].
Anselmi, E ;
Blazejewski, JC ;
Tordeux, M ;
Wakselman, C .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 105 (01) :41-44
[2]   Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis [J].
Arimori, Sadayuki ;
Matsubara, Okiya ;
Takada, Masahiro ;
Shiro, Motoo ;
Shibata, Norio .
ROYAL SOCIETY OPEN SCIENCE, 2016, 3 (05)
[3]  
Asakura S., 2012, Pakistan Journal of Weed Science Research, V18, P719
[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]   Late stage trifluoromethylthiolation strategies for organic compounds [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio ;
Postigo, Al .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) :7150-7182
[6]   Synthesis of Difluoromethyl Thioethers from Difluoromethyl Trimethylsilane and Organothiocyanates Generated In Situ [J].
Bayarmagnai, Bilguun ;
Matheis, Christian ;
Jouvin, Kevin ;
Goossen, Lukas J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5753-5756
[7]   Fluorinated ylides and related compounds [J].
Burton, DJ ;
Yang, ZY ;
Qiu, WM .
CHEMICAL REVIEWS, 1996, 96 (05) :1641-1715
[8]   Visible Light-Promoted Decarboxylative Di- and Trifluoromethylthiolation of Alkyl Carboxylic Acids [J].
Candish, Lisa ;
Pitzer, Lena ;
Gomez-Suarez, Adrian ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (14) :4753-4756
[9]   State-of-the-Art in Electrophilic Trifluoromethylthiolation Reagents [J].
Chachignon, Helene ;
Cahard, Dominique .
CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (05) :445-454
[10]   Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].
Chatterjee, Tanmay ;
Iqbal, Naeem ;
You, Youngmin ;
Cho, Eun Jin .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294