Stille cross-coupling of activated alkyltin reagents under "ligandless" conditions

Monoalkyltins activated by a fluoride source are shown to be as reactive as their vinyl or aryl homologues in the Stille coupling reaction, thus providing an easy entry into the pallado-catalyzed formation of Csp3-Csp2 bonds. In addition to this uncommon reactivity, this methodology holds several advantages such as (i) a quantitative preparation of stable and easy to handle alkyltin reagents 2, (ii) a simplified coupling procedure without any phosphine added ligand under neutral conditions, and (iii) a facile purification step of the organic products from the inorganic nontoxic tin byproducts.