A one-pot azido reductive tandem mono-N-alkylation employing dialkylboron triflates: online ESI-MS mechanistic investigation.

An efficient one-pot reductive tandem mono-N-alkylation of both aromatic and aliphatic azides using dialkylboron triflates as alkylating agents has been examined under standardized reaction conditions. This methodology after optimization has been employed toward the syntheses of various secondary alkyl as well as aryl amines, including the synthesis of N10-butylated pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via in situ azido reductive-cyclization process. This protocol is particularly attractive to provide an environmentally benign and practical method for mono-N-alkylation from organic azides without the use of toxic catalysts or corrosive alkylating agents.