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Use of Trifluoromethyl Groups for Catalytic Benzylation and Alkylation with Subsequent Hydrodefluorination
Author(s) -
Zhu Jiangtao,
Pérez Manuel,
Caputo Christopher B.,
Stephan Douglas W.
Publication year - 2016
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.201510494
Subject(s) - alkylation , chemistry , aryl , alkyl , electrophile , trifluoromethyl , catalysis , medicinal chemistry , friedel–crafts reaction , organic chemistry
The electrophilic organofluorophosphonium catalyst [(C 6 F 5 ) 3 PF][B(C 6 F 5 ) 4 ] is shown to effect benzylation or alkylation by aryl and alkyl CF 3 groups with subsequent hydrodefluorination, thus resulting in a net transformation of CF 3 into CH 2 –aryl fragments. In the case of alkyl CF 3 groups, Friedel–Crafts alkylation by the difluorocarbocation proceeded without cation rearrangement, in contrast to the corresponding reactions of alkyl monofluorides.