Photocatalytic Diazo‐Transfer from Hypervalent Iodine Diazo Reagents to Azocarboxylates: Divergent Access to 1H‐Diazirines and 1H‐Tetrazoles

Abstract

The diazo‐group transfer from hypervalent iodine diazo reagents to azocarboxylates under photocatalytic conditions is reported. The subsequent intramolecular decarboxylative cyclization leads to the divergent access to 1H‐diazirines and 1H‐tetrazoles depending upon the substituents in the azo‐substrate. The control experiments suggest that the diazo‐group transfer may take place through photocatalytically generated diazomethyl radical intermediate or through electrophilic diazomethylation of azocarboxylate radical anion.