Mechanism of hydrogenolysis. Part 1. Catalytic hydrogenation of vinyl and aryltrifluoromethanesulphonates

Abstract

A concerted cleavage of the C–O bond by the MH₂ species is proposed for the first step of the catalytic hydrogenation of vinyl and aryl trifluoromethanesulphonates. The alkene thus generated in the case of vinyl trifluoromethanesulphonates, is subsequently, reduced to an alkane. The stereochemistry of the reduction of vinyl trifluoromethanesulphonates is therefore identical to that observed in the reduction of the corresponding alkenes.