Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes

被引:56
作者
He, Lisi [1 ]
Tsui, Gavin Chit [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; ARYL BORONIC ACIDS; NUCLEOPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; DIRECT CUPRATION; MEDIATED TRIFLUOROMETHYLATION; EFFICIENT PRECURSOR; CARBONYL-COMPOUNDS; FLUORINE; DIFLUOROMETHYLATION;
D O I
10.1021/acs.orglett.6b00999
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
引用
收藏
页码:2800 / 2803
页数:4
相关论文
共 67 条
[1]   α-Difluoromethylation on sp3 Carbon of Nitriles Using Fluoroform and Ruppert-Prakash Reagent [J].
Aikawa, Kohsuke ;
Maruyama, Kenichi ;
Honda, Kazuya ;
Mikami, Koichi .
ORGANIC LETTERS, 2015, 17 (19) :4882-4885
[2]   Coupling of fluoroform with aldehydes using an electrogenerated base [J].
Barhdadi, R ;
Troupel, M ;
Périchon, J .
CHEMICAL COMMUNICATIONS, 1998, (12) :1251-1252
[3]   Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845
[4]   New stable reagents for the nucleophilic trifluoromethylation.: 1.: Trifluoromethylation of carbonyl compounds with N-formylmorpholine derivatives [J].
Billard, T ;
Bruns, S ;
Langlois, BR .
ORGANIC LETTERS, 2000, 2 (14) :2101-2103
[5]   Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry [J].
Brisdon, AK ;
Crossley, IR .
CHEMICAL COMMUNICATIONS, 2002, (20) :2420-2421
[6]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[7]   Net Oxidative Addition of C(sp3)-F Bonds to Iridium via Initial C-H Bond Activation [J].
Choi, Jongwook ;
Wang, David Y. ;
Kundu, Sabuj ;
Choliy, Yuriy ;
Emge, Thomas J. ;
Krogh-Jespersen, Karsten ;
Goldman, Alan S. .
SCIENCE, 2011, 332 (6037) :1545-1548
[8]   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
[9]   Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+
[10]   Fluoroform:: An efficient precursor for the trifluoromethylation of aldehydes [J].
Folléas, B ;
Marek, I ;
Normant, JF ;
Saint Jalmes, L .
TETRAHEDRON LETTERS, 1998, 39 (19) :2973-2976