Premium
Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles
Author(s) -
Egami Hiromichi,
Shimizu Ryo,
Kawamura Shintaro,
Sodeoka Mikiko
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201210250
Subject(s) - trifluoromethylation , allylic rearrangement , alkene , chemistry , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , trifluoromethyl , alkyl
The combo pack : Copper‐catalyzed trifluoromethylation of alkenes bearing an allylic proton combined with CC bond formation affords the title compounds in good to high yields (see scheme). The reactions are faster than allylic trifluoromethylation, especially in 1,4‐dioxane. A unique 1,6‐oxytrifluoromethylation occurred instead of an anticipated seven‐membered ring forming carbotrifluoromethylation reaction.