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.
International audienceThe synthesis of a new series of arylhydroxymethylphosphinic acid derivatives is described. The protected compounds were prepared by a palladium(0) catalysed arylation of ethyl benzyloxymethylphosphinate with aryl halides. Subsequent hydrogenolysis of the benzyl protecting group followed by acidic hydrolysis of the ester function readily afforded the target compounds. Selective removal of the ester group was achieved by basic hydrolysis whereas acidic hydrolysis directly gave the totally deprotected compounds
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