OsO4-Mediated Conversion of Primary Amines to Nitriles

Nitriles are very important intermediates in synthetic organic chemistry. Herein, we report our observation that certain primary amines can be converted to nitriles by trimethylamine N-oxide (TMO) under mild conditions in the presence of a catalytic amount of OsO4. Such a reaction could be used for synthetic purposes as well as for the analysis of functional group compatibility in designing reactions involving OsO4.