SnCl2 mediated efficient N,N-dialkylation of azides to tertiary-amine via potential stannaimine intermediate

A base free one-pot conversion of azides to N,N-dialkylamine is described. A two-step reaction pathway has been postulated invoking the intermediacy of stannaimine. This new carbon–nitrogen bond formation strategy adds to the repertoire of tin(II) chemistry.

Under the aegis of anhydrous stannous chloride, the reaction of aliphatic or aromatic azides with organic halides (alkyl, benzyl, propargyl) lead to the formation of corresponding N,N-dialkylamines in good to excellent yields. Additional Pd(0) catalyst further enhances the yield in the case of allyl halides. The intermediacy of reactive stannaimine is postulated for this new base free C–N bond forming strategy.Figure optionsDownload as PowerPoint slide