Palladium-Catalyzed Difluoromethylation of Aryl Chlorides and Bromides with TMSCF2H

被引:36
作者
Ferguson, Devin M. [1 ]
Malapit, Christian A. [1 ]
Bour, James R. [1 ]
Sanford, Melanie S. [1 ]
机构
[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48109 USA
关键词
COPPER-MEDIATED DIFLUOROMETHYLATION; FLUORINE; REAGENT; IODIDES; HALIDES; TRIFLUOROMETHYLATION; COUPLINGS; ARENES; ACIDS;
D O I
10.1021/acs.joc.9b00324
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed cross-coupling of aryl chlorides/bromides with TMSCF2H is described. Two different catalysts, Pd(dba)(2)/BrettPhos and Pd((PBu3)-Bu-t)(2), are demonstrated and provide a variety of difluoromethylated arenes in good yields.
引用
收藏
页码:3735 / 3740
页数:6
相关论文
共 41 条
[1]   Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent [J].
Aikawa, Kohsuke ;
Serizawa, Hiroki ;
Ishii, Koki ;
Mikami, Koichi .
ORGANIC LETTERS, 2016, 18 (15) :3690-3693
[2]   Metallaphotoredox Difluoromethylation of Aryl Bromides [J].
Bacauanu, Vlad ;
Cardinal, Sebastien ;
Yamauchi, Motoshi ;
Kondo, Masaru ;
Fernandez, David F. ;
Remy, Richard ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) :12543-12548
[3]   Synthesis, Reactivity, and Catalytic Applications of Isolable (NHC)Cu(CHF2) Complexes [J].
Bour, James R. ;
Kariofillis, Stavros K. ;
Sanford, Melanie S. .
ORGANOMETALLICS, 2017, 36 (07) :1220-1223
[4]   Transition-Metal-Catalyzed Difluoromethylation, Difluoromethylenation, and Polydifluoromethylenation Reactions [J].
Chen, Bo ;
Vicic, David A. .
ORGANOMETALLIC FLUORINE CHEMISTRY, 2015, 52 :113-141
[5]   Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations [J].
Chen, Pinhong ;
Liu, Guosheng .
SYNTHESIS-STUTTGART, 2013, 45 (21) :2919-2939
[6]   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
[7]   C-F Bond Activation of P(C6F5)3 by Ruthenium Dihydride Complexes: Isolation and Reactivity of the "Missing" Ru(PPh3)3H(halide) Complex, Ru(PPh3)3HF [J].
Cybulski, Mateusz K. ;
Davies, Caroline J. E. ;
Lowe, John P. ;
Mahon, Mary F. ;
Whittlesey, Michael K. .
INORGANIC CHEMISTRY, 2018, 57 (21) :13749-13760
[8]   HYDROGEN-BOND DONOR PROPERTIES OF THE DIFLUOROMETHYL GROUP [J].
ERICKSON, JA ;
MCLOUGHLIN, JI .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1626-1631
[9]  
Feng Z, 2017, NAT CHEM, V9, P918, DOI [10.1038/NCHEM.2746, 10.1038/nchem.2746]
[10]   Access to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate [J].
Feng, Zhang ;
Min, Qiao-Qiao ;
Zhang, Xingang .
ORGANIC LETTERS, 2016, 18 (01) :44-47