Enhancing reductive cleavage of aromatic carboxamides

[GRAPHICS] A set of aromatic and especially heteroaromatic N-benzyl carboxamides, deri ved from naphthalene, pyridine, pyrazine, and quinoline, and the correspond ing tert-butyl acylcarbamates have been synthesized and studied by cyclic v oltammetry with respect to facilitated reduction. The latter undergo regios pecific cleavage of their C(O)-N bonds under very mild reductive conditions with formation of Boc-protected (benzyl)amine in most cases in nearly quan titative yields, Examples of preparative cleavage by controlled potential e lectrolysis, activated aluminum, and NaBH4 are given.