Synthesis of α-tribromomethylamines via Mg-mediated addition of bromoform to imines

Abstract

Mg-mediated addition of bromoform to electron deficient imines such as N-sulfonylimines affords α-tribromomethylated N-sulfonylamines in good to excellent yields. The procedure could be further simplified by transforming the imine precursors, α-sulfonyl-N-tosyl- and Boc-amines, in one pot to the corresponding α-tribromomethyl derivatives. Facile removal of the Boc protecting group in nearly quantitative yield and a silver carbonate mediated monodebromination have also been demonstrated.