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

In presence of catalytic Pd(0) or Pt(II), a reagent combination of SnCl2-LiOH promotes the reaction of organic halides and epoxides in dichloromethane leading to the regioselective formation of corresponding homoallyl and homopropargyl alcohols in good yields. This 2-carbon extension strategy adds to the repertoire of Barbier reactions via metal salts and reinforces views on the enhanced reactivity of organotin having -OH pendant. (c) 2004 Elsevier B.V. All rights reserved.