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Dr. Nicholas A. Phillips Gregory J. Coates Dr. Andrew J. P. White Dr. Mark R. Crimmin 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(24):5365-5368
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 sp3 C−F bond of a CF3 group in the presence of sp2 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 (SN2’) but electrophilic at boron en route to the carbon–carbon bond-forming step (SE2’). The duplicitous behaviour is underpinned by a hydrogen atom migration from boron to the carbon atom of a carbene ligand. 相似文献
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