Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 24, Pages 5365-5368Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000636
Keywords
C-F functionalisation; defluoroalkylation; fluorine; HFOs; trifluoromethyl
Categories
Funding
- European Research Council [FluoroFix:677367]
- EPSRC
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A simple, one-pot procedure is reported for the selective defluoroalkylation of trifluoromethyl alkene derivatives with aldehydes and ketones. The reaction sequence allows construction of a new C-C bond in a highly selective manner from a single sp(3) C-F bond of a CF3 group in the presence of sp(2) C-F bonds. The scope incorporates industrially relevant fluorocarbons including HFO-1234yf and HFO-1234ze. No catalyst, additives or transition metals are required, rather the methodology relies on a recently developed boron reagent. Remarkably, the boron site of this reagent plays a dual role in the reaction sequence, being nucleophilic at boron in the C-F cleavage step (S(N)2') but electrophilic at boron en route to the carbon-carbon bond-forming step (S(E)2'). The duplicitous behaviour is underpinned by a hydrogen atom migration from boron to the carbon atom of a carbene ligand.
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