We report the development of a general Pd-catalyzed process for the stereoretentive cross-coupling of secondary alkyl azastannatrane nucleophiles and aryl electrophiles. This reaction displays no dependence on the electronic characteristics of either coupling partner and occurs with minimal concurrent isomerization of the secondary alkyltin nucleophile. Aryl chlorides, bromides, iodides, and triflates are all viable electrophiles in this process. Additionally, optically-active secondary alkyl azastannatranes undergo cross-coupling reactions with retention of absolute configuration using this method. This process constitutes the first general method to employ secondary alkyltin reagents in cross-coupling reactions. Overall, the combined generality of the transformation and stability of optically-active azastannatranes result in a process that should accommodate the broad use of optically-active nucleophiles.

Stereoretentive Pd-catalyzed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides

246th National Meeting (2013)

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