Amine-boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization.

The first general open-flask synthesis of amine-boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine-boranes represent stable molecules containing potentially incompatible electrophilic and nucleophilic centers in proximity. This convenient scalable synthesis provides a novel class of organic ligands for surface functionalization, as demonstrated by the formation of self-assembled layers of thiol- and alkoxysilane-bearing amine-boranes on gold and silica surfaces, respectively.