π‐Conjugated Triazenes and Nitriles: Simple Photoinduced Synthesis of Anilides Using Mild and Metal‐Free Conditions

Abstract

A simple, clean, direct, photochemical, and metal‐free approach to produce structurally diverse anilides in good to excellent yields (up to 99%), by utilizing π‐conjugated triazene reactivity and simple nitriles is presented. Interestingly, natural sunlight is also shown to provide effective delivery of amides, with yields up to 99%.

Photo‐Driven Direct C−H Arylation of Quinoxalin‐2(1H)‐Ones with Aryltriazenes under Catalyst‐Free and Ambient Conditions

“…However, the involvement of equivalent acid promoter would decrease the selectivity and functional group tolerance of the aforementioned reaction. Alternatively, a few catalytic [9] and photo‐induced [10] reactions of aryltriazenes have been reported in recent years (Scheme 1b), however, the use of noble metal catalysts at high temperatures, [9] π‐conjugated triazenes as substrate, [10a,b] high‐energy UV light irradiation, [10c] and the combination with weak acid additives [10a,b] allows room for further improvement. Based on our continual study on the development of safe and sustainable organic synthesis methodology with easily available aryltriazenes and photo‐catalysis, [8a,b,f,g,o,p,9e,11] herein, we present a facile photo‐induced direct C−H arylation of quinoxalin‐2(1 H )‐ones with aryltriazenes under promoter‐, metal‐, photocatalyst‐ and oxidant‐free conditions (Scheme 1c).…”