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Dual Catalysis with Copper and Rhenium for Trifluoromethylation of Propargylic Alcohols: Efficient Synthesis of α‐Trifluoromethylated Enones
Author(s) -
Egami Hiromichi,
Ide Takafumi,
Fujita Masashi,
Tojo Toshifumi,
Hamashima Yoshitaka,
Sodeoka Mikiko
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403447
Subject(s) - trifluoromethylation , chemistry , yield (engineering) , steric effects , rhenium , catalysis , selectivity , copper , organic chemistry , medicinal chemistry , combinatorial chemistry , trifluoromethyl , alkyl , materials science , metallurgy
Abstract Trifluoromethylation of propargylic alcohols to provide ( Z )‐α‐trifluoromethylated enones and β‐unsubstituted α‐trifluoromethylated enones proceeded with high yield and selectivity in the presence of CuI/Re 2 O 7 . The Z isomer was formed under kinetic control, though it is less stable than the E isomer in terms of steric repulsion.