Metal-Free Visible-Light Catalytic Deoxygenation of Azaaryl N-Oxides: Harnessing Photons for Efficient Greener Synthesis.

Abstract

Regio- and chemo-selective functionalization of electron deficient azaarenes often required their transformations to corresponding N-oxides and subsequent removal of oxygen after functionalization to get back the desired substituted azaarenes. An efficient metal-free visible-light photo-redox catalytic deoxygenation of N-oxides of azaheterocyclic compounds has been developed using acridinium based organo-photocatalyst in blue LED light. High efficiency and mildness of this methodology has been demonstrated through higher deoxygenation yield of wide variety of azaheterocyclic N-oxides with reactive functional groups. Robustness of the photocatalytic reduction has been demonstrated through easy scaling-up of the reaction to gram level without much change in the reaction yield.