Nucleophilic fluoroalkylation of (bromomethyl)pinacolborane using silicon reagents

A method for the synthesis of pinacol boronic esters bearing a fluorinated group at the a-carbon atom (R(f)CH(2)Bpin) from corresponding bromomethyl borane (BrCH(2)Bpin) and fluorinated silanes (RfSiMe3) is described. The fluoroalkylation reaction involves formation of borate anions followed by intramolecular nucleophilic substitution of bromine. (C) 2013 Elsevier B.V. All rights reserved.