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Copper‐Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Generation of a CCF 3 Bond from an O‐Based Electrophile
Author(s) -
Zhu Lingui,
Liu Shasha,
Douglas Justin T.,
Altman Ryan A.
Publication year - 2013
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.201302328
Subject(s) - trifluoromethylation , electrophile , chemistry , trifluoromethyl , reagent , copper , substrate (aquarium) , functional group , alcohol , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl , geology , oceanography , polymer
The conversion of an alcohol‐based functional group, into a trifluoromethyl analogue is a desirable transformation. However, few methods are capable of converting O‐based electrophiles into trifluoromethanes. The copper‐mediated trifluoromethylation of benzylic xanthates using Umemoto’s reagent as the source of CF 3 to form CCF 3 bonds is described. The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the CCF 3 bond forms by reaction of the substrate with in situ generated CuCF 3 and CuOTf. Further evidence suggests that the reaction could proceed via a radical cation intermediate.