Manganese-Catalyzed Late-Stage Aliphatic C-H Azidation

We report a manganese-catalyzed aliphatic azidation reaction that can, efficiently :Convert secondary, tertiary, and benzylic C-H bonds to the corresponding azides. The;method utilizes aqueous sodium azide solution as the azide source and can be performed under air. Besides its operational simplicity, the potential of this method for late-stage functionalization has been demonstrated by successful azidation of various, bioactive molecules, With yields up to 74%, including the important,drugs pregabalin, memantine, and the anti-malarial Azidation of celestolide with a chiral manganese salen catalyst afforded the azide product in 70% ee, representing a Mn-catalyzed enantioselective aliphatic C-H azidation reaction. Considering the versatile roles of organic aides in modem chemistry and the ubiquity of aliphatic C-H bond's in Organic molecules, We envision that this Mn-azidation method will find wide application in organic synthesis; drug discovery, and chemical biology.