Tuning the reactivity of organotin(IV) by LiOH: allylation and propargylation of epoxides via redox transmetalation

Nucleophilic reactivity of organotin is enhanced by stoichiometric LiOH to give homoallyl and homopropargyl alcohols from allyl halide and arylepoxide under the aegis of catalytic Pd(0) and Pt(II). This 2-carbon extension strategy proceeds via tandem epoxide rearrangement-carbonyl addition and further reinforces earlier views on the enhanced reactivity of hydroxy derivatives of organotin such as RSnXn(OH)3 − n.