title: Use of Trifluoromethyl Groups for Catalytic Benzylation and Alkylation with Subsequent Hydrodefluorination.
abstract: The electrophilic organofluorophosphonium catalyst [(C6F5)3PF][B(C6F5)4] is shown to effect benzylation or alkylation by aryl and alkyl CF3 groups with subsequent hydrodefluorination, thus resulting in a net transformation of CF3 into CH2-aryl fragments. In the case of alkyl CF3 groups, Friedel-Crafts alkylation by the difluorocarbocation proceeded without cation rearrangement, in contrast to the corresponding reactions of alkyl monofluorides.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Jiangtao
authors.initials: J
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Manuel
authors.initials: M
authors.lastname: Pérez
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Christopher B
authors.initials: CB
authors.lastname: Caputo
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. dstephan@chem.utoronto.ca.
authors.forename: Douglas W
authors.identifier: http://orcid.org/0000-0001-8140-8355
authors.initials: DW
authors.lastname: Stephan
keywords: alkylation; benzylation; electrophilic phosphonium cations; hydrodefluorination; trifluoromethyl groups