Iron-catalyzed Azidation of Cyclobutanol by C C Bond Cleavage

An iron-catalyzed ring-opening azidation of cyclobutanols through CC bond cleavage is disclosed for the first time. A range of tertiary cyclobutanols are tolerated providing γ-carbonyl-containing secondary alkyl azides. The method provides a straightforward approach for introducing azide group into aliphatic chain of organic molecules. A plausible mechanism involving radical-mediated sequential CC bond cleavage and C−N3 bond formation is proposed.