Open AccessTrifluoromethylation of Propargylic Halides and Trifluoroacetates Using (Ph3P)3Cu(CF3) Reagent
Author(s) -
Tony S. N. Zhao,
Kálmán J. Szabó
Publication year - 2012
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol3017287
Subject(s) - chemistry , trifluoromethylation , reagent , nucleophile , halide , propargyl , ionic bonding , medicinal chemistry , substrate (aquarium) , selectivity , copper , organic chemistry , combinatorial chemistry , trifluoromethyl , catalysis , ion , alkyl , oceanography , geology
A copper-mediated trifluoromethylation of propargylic halides and trifluoroacetates was performed with high allenyl or propargyl selectivity. The reaction proceeds smoothly with aliphatic and aromatic substituents bearing either electron-withdrawing or -supplying groups. Preliminary mechanistic results indicate an ionic mechanism involving nucleophilic transfer of the CF(3) group from the Cu complex to the propargylic substrate.