Dirhodium(II)-Catalyzed C(sp2 )-H Azidation of Benzaldehydes.

Abstract

Multiple steps are needed to achieve the C-H functional of aromatic aldehyde, since the C-H functional reaction usually occurs preferentially at the aldehydic C-H bond over the aryl C-H bond. We report an efficient azidation method mediated by dirhodium(II) catalysts to achieve the direct aryl azidation of aromatic aldehydes avoiding the simultaneous use of protected aldehydes and prefunctionalized arenes. The regioselectivity of this method is similar to those of typical aromatic electrophilic substitution reactions. The resulting azidobenzaldehyde products are versatile building blocks or precursors for the synthesis of many biologically active compounds. The mechanism studies indicate that the one-electron oxidative intermediate Rh2 (II,III) N3 is responsible for the azide transfer.