Direct C–H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis
Guiqing Xu, Jiayuan Lv, Qingjie Ding, Chunhua Ma, Yuqin Jiang, Bing Yu
Abstract
2,1,3-Benzothiadiazole is widely used as a privileged scaffold in pharmaceuticals and organic functional materials. Nonetheless, many current methods for the functionalization of 2,1,3-benzothiadiazole rely on preactivation, transition metal catalysts/promoters, or an elevated reaction temperature. Herein we disclose a transition-metal-free visible-light-induced photocatalytic method for the direct C–H alkylation of 2,1,3-benzothiadiazole using readily accessible carboxylic acid derivatives, i.e., N -hydroxyphthalimide esters (NHPEs), as alkylating reagents under room temperature. This mild and scalable method is highlighted by the late-stage installation of the benzothiadiazole scaffold in drugs and natural products.