A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines

We report the development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines with exquisite site- and chemoselectivity. The novel reagent was prepared on 200 gram-scale in a single step, reacts in the title reaction under mild conditions without precautions towards air or moisture, and is tolerant of nearly all common functionality. Experimental and in-situ spectroscopic monitoring techniques provide detailed insights and unexpected findings for the unique reaction mechanism.