Convenient Synthesis of Salicylanilide Sulfonates from 1,2,3-Benzotriazin-4(3H)-ones and Organosulfonic Acids via Denitrogenative Cross-Coupling

An efficient and straightforward approach to synthesize salicylanilide aryl and alkyl sulfonates from 1,2,3-benzotriazin-4(3H)-ones and organosulfonic acids is described. This protocol is operationally simple and scalable, exhibits a broad substrate scope with high functional group tolerance, and affords the desired products in good to high yield. Application of the reaction is also demonstrated by converting the desired product to synthetically useful salicylamides in high yields.

Automated summary

An efficient and straightforward method for the synthesis of salicylanilide aryl and alkyl sulfonates from 1,2,3-benzotriazin-4(3H)-ones and organosulfonic acids is presented. The protocol is simple to perform and can be easily scaled up. It has a broad substrate scope with high tolerance towards functional groups, and provides the desired products in good to high yield. The application of the reaction is demonstrated by converting the desired product to salicylamides with high yields.