The regiochemical influence of oxo-substitution in palladium-mediated hydrostannations of 1-alkynes

A systematic study of hydroxyalkynes and their derivatives showed that the presence and position of the oxygen functionality can influence the regiose lectivity of their Pd(0)-catalyzed and free radical hydrostannations. Regio selectivity is influenced by functional group proximity, sterics, and the n ature of the substituent (hydroxyl, ether, or ester). Information provided herein may be useful when deciding which methodology and/or protective grou p strategy to employ when forming vinylstannanes.