Synthesis, Reactivity, and Catalytic Applications of Isolable (NHC)Cu(CHF2) Complexes

被引:68
作者
Bour, James R. [1 ]
Kariofillis, Stavros K. [1 ]
Sanford, Melanie S. [1 ]
机构
[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48109 USA
基金
美国国家科学基金会;
关键词
COPPER-MEDIATED DIFLUOROMETHYLATION; BURIED VOLUME; ARYL BROMIDES; HALIDES; TRIFLUOROMETHYLATION; ALLYLATION; LIGANDS; IODIDES; ACCESS;
D O I
10.1021/acs.organomet.7b00025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Difluoromethyl copper complexes have been proposed as key intermediates in a variety of Cu-catalyzed difluoromethylation reactions. However, studies of these putative intermediates have been impeded by the low stability of these [Cu(CHF2)] species. This report describes the synthesis of isolable N-heterocyclic carbene ligated copper(I) difluoromethyl complexes. The stoichiometric reactions of these complexes with aryl electrophiles (i.e., diaryliodonium salts, aryl iodides, and aryl bromides) are described. In addition, N-heterocyclic carbene copper(I) species are demonstrated to serve as catalysts for the cross-coupling of aryl iodides with (difluoromethyl)trimethylsilane to afford difluoromethyl arene products.
引用
收藏
页码:1220 / 1223
页数:4
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