“Propylene spaced” allyl tin reagents: A new class of fluorous tin reagents for allylations under radical and metal-catalyzed conditions

A new generation of propylene-spaced fluorous allyltin reagents [(Rf(CH2)3)3SnCH2CH=CH2] is described. These succeed in radical allylations where their lower homologs (ethylene-spaced) fail, and they provide improved performance in transition metal catalyzed allylations. The reagents and byproducts are readily separated by simple fluorous-organic liquid-liquid or solid-liquid extractions.