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Palladium‐Catalyzed Cascade CH Trifluoroethylation of Aryl Iodides and Heck Reaction: Efficient Synthesis of ortho ‐Trifluoroethylstyrenes
Author(s) -
Zhang Hao,
Chen Pinhong,
Liu Guosheng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403793
Subject(s) - chemistry , palladium , reductive elimination , aryl , oxidative addition , heck reaction , catalysis , reactivity (psychology) , medicinal chemistry , cascade reaction , combinatorial chemistry , organic chemistry , medicine , alkyl , alternative medicine , pathology
A palladium‐catalyzed selective CH bond trifluoroethylation of aryl iodides has been explored. The reaction allows for the efficient synthesis of a variety of ortho ‐trifluoroethyl‐substituted styrenes. Preliminary mechanistic studies indicate that the reaction might involve a key Pd IV intermediate, which is generated through the rate‐determining oxidative addition of CF 3 CH 2 I to a palladacycle; the bulky nature of CF 3 CH 2 I influences the reactivity. Reductive elimination from the Pd IV complex then leads to the formation of the aryl–CH 2 CF 3 bond.