A Trifluoromethylcarbene Source

被引:44
作者
Duan, Yaya [1 ]
Lin, Jin-Hong [1 ]
Xiao, Ji-Chang [1 ]
Gu, Yu-Cheng [2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
关键词
DIASTEREOSELECTIVE SYNTHESIS; CATALYZED CYCLOPROPANATION; SELECTIVE OLEFINATION; IRON PORPHYRIN; ALDEHYDES; DIFLUOROCARBENE; FLUORINE; IMIDAZOPYRIDINES; DECOMPOSITION;
D O I
10.1021/acs.orglett.6b01042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trifluoromethylcarbene (:CHCF3) was found to be conveniently generated from (2,2,2-trifluoroethyl)diphenyl-sulfonium triflate (Ph2S+CH2CF3 -OTf, which was successfully applied in Fe-catalyzed cyclopropanation of olefins, giving the corresponding trifluoromethylated cyclopropanes in high yields.
引用
收藏
页码:2471 / 2474
页数:4
相关论文
共 58 条
[1]  
Abraham S, 2009, PCT Int Appl, Patent No. [WO 2009117080 A1, 2009117080]
[2]   Synthesis and Applications of α-Trifluoromethylated Alkylboron Compounds [J].
Argintaru, O. Andreea ;
Ryu, DaWeon ;
Aron, Ioana ;
Molander, Gary A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (51) :13656-13660
[3]   Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].
Arrayas, Ramon Gomez ;
Adrio, Javier ;
Carretero, Juan Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715
[4]   INSERTION REACTIONS OF TRIFLUOROMETHYLCARBENE [J].
ATHERTON, JH ;
FIELDS, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (18) :2276-&
[5]   The syntheses and catalytic applications of unsymmetrical ferrocene ligands [J].
Atkinson, RCJ ;
Gibson, VC ;
Long, NJ .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :313-328
[6]   Metabolically Stable tert-Butyl Replacement [J].
Barnes-Seeman, David ;
Jain, Monish ;
Bell, Leslie ;
Ferreira, Suzie ;
Cohen, Scott ;
Chen, Xiao-Hui ;
Amin, Jakal ;
Snodgrass, Brad ;
Hatsis, Panos .
ACS MEDICINAL CHEMISTRY LETTERS, 2013, 4 (06) :514-516
[7]   Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions [J].
Burtoloso, Antonio C. B. ;
Dias, Rafael M. P. ;
Leonarczyk, Ives A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) :5005-5016
[8]   Copper-triggered three-component reaction of CF3CHN2, nitriles, and aldehydes: highly diastereoselective synthesis of CF3-substituted oxazolines and vicinal amino alcohols [J].
Cai, Ai-Jie ;
Zheng, Yan ;
Ma, Jun-An .
CHEMICAL COMMUNICATIONS, 2015, 51 (43) :8946-8949
[9]   Chiral Bronsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines [J].
Chai, Zhuo ;
Bouillon, Jean-Philippe ;
Cahard, Dominique .
CHEMICAL COMMUNICATIONS, 2012, 48 (76) :9471-9473
[10]   Iron(III) and ruthenium(II) porphyrin complex-catalyzed selective olefination of aldehydes with ethyl diazoacetate [J].
Chen, Y ;
Huang, L ;
Ranade, MA ;
Zhang, XP .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3714-3717