Activation of Alkyl C–F Bonds by B(C6F5)3: Stoichiometric and Catalytic Transformations
The Lewis acid B(C 6 F 5 ) 3 is shown to activate a series of alkyl fluorides. In stoichiometric reactions, treatment of sterically demanding phosphines with B(C 6 F 5 ) 3 /alkyl fluorides gives phosphonium fluoroborate salts while treatment of B(C 6 F 5 ) 3 /alkyl fluorides with the salts [ t Bu 3 PX][XB(C 6 F 5 ) 3 ] (X = H, PhS) gives the alkane and the salt byproduct [ t Bu 3 PX][FB(C 6 F 5 ) 3 ]. These fluoroalkanes are also catalytically converted to the corresponding alkanes by reaction of the fluoroalkane and Et 3 SiH using B(C 6 F 5 ) 3 as the catalyst.