Remote Radical Azidation of Unactivated C(sp 3 )-H Bonds in Sulfamoyl Azides.

An efficient method for remote radical C(sp 3 )-H azidation at unactivated sites is described. C-H functionalization proceeds via intramolecular 1,5-hydrogen atom transfer to N-centered radicals that are generated via azido group transfer and/or fragmentation. The readily installed sulfamoyl azide serves as both an amidyl radical precursor and an azido source. This reaction features excellent site selectivity for tertiary, secondary, primary, and benzylic C(sp 3 )-H bonds and exhibits broad functional group compatibility.