Palladium-catalyzed difluoromethylthiolation of heteroaryl bromides, iodides, triflates and aryl iodides

被引:55
作者
Wu, Jiang [1 ]
Liu, Yafei [1 ]
Lu, Changhui [1 ]
Shen, Qilong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-FLUORINATED ETHERS; MEDICINAL CHEMISTRY; DIRECT DIFLUOROMETHYLATION; C-NUCLEOPHILES; THIOETHERS; ARYLATION; REAGENT; HETEROCYCLES; COMPLEXES; HALIDES;
D O I
10.1039/c6sc00082g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed difluoromethylthiolation of heteroaryl halides and triflates under mild conditions was described. A vast range of heteroaryl halides such as pyridyl, quinolinyl, benzothiazolyl, thiophenyl, carbazolyl and pyazolyl halides could be difluoromethylthiolated efficiently, thus providing medicinal chemists with new tools for their search of new lead compounds for drug discovery. Likewise, aryl iodides were difluoromethylthiolated in high yields under a modified reaction condition.
引用
收藏
页码:3757 / 3762
页数:6
相关论文
共 52 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]  
Amrein J., 1989, BRIGHT CROP PROT C W, V1, P71
[3]   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
[4]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[5]  
de Meijere A., 2010, METAL CATALYZED CROS
[6]   Taming Hazardous Chemistry in Flow: The Continuous Processing of Diazo and Diazonium Compounds [J].
Deadman, Benjamin J. ;
Collins, Stuart G. ;
Maguire, Anita R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) :2298-2308
[7]   Synthesis of difluoromethylthio imidazole from methylthio imidazole [J].
Deprez, P ;
Vevert, JP .
JOURNAL OF FLUORINE CHEMISTRY, 1996, 80 (02) :159-162
[8]   Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds [J].
Fuchibe, Kohei ;
Bando, Masaki ;
Takayama, Ryo ;
Ichikawa, Junji .
JOURNAL OF FLUORINE CHEMISTRY, 2015, 171 :133-138
[9]   NEW SUBSTITUENT CONSTANT PI DERIVED FROM PARTITION COEFFICIENTS [J].
FUJITA, T ;
HANSCH, C ;
IWASA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5175-&
[10]   A New Reagent for Direct Difluoromethylation [J].
Fujiwara, Yuta ;
Dixon, Janice A. ;
Rodriguez, Rodrigo A. ;
Baxter, Ryan D. ;
Dixon, Darryl D. ;
Collins, Michael R. ;
Blackmond, Donna G. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1494-1497