Development of novel and efficient synthetic methods to achieve valuable N-heterocycles from aryldiazonium salts has been an important research area in organic chemistry for several decades.
The UV-activated peracetic acid process (UV/PAA) exhibited efficient degradation and detoxification of benzotriazole (BT) and benzothiazole (BTH). Detailed mechanistic insights into the UV/PAA degradation of BT and BTH have been thoroughly explored.
We described a visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole to generate unusual aromatic amine radical which then undergo direct amination with quinoxalin-2(1H)-ones leading to 3-aryl-aminoquinoxalin-2(1H)-ones.
n Bu4NI serves as both electrolyte and iodine mediator in the method, which is characterized by its simple operation (undivided electrolytic cells at room temperature), good atom efficiency, and eco-friendliness, with hydrogen as the sole byproduct.
A Lewis acid-switching strategy that enables programmable selectivity between kinetically controlled N1-alkylation and thermodynamically favored N2-alkylation using β-hydroxy-α-diazo carbonyls as versatile electrophiles has been disclosed.