B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N-1 and N-2 alkylation. Herein, metal-free catalytic site-selective N-1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)(3). These reactions provide N-1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Automated summary

The study demonstrates a metal-free catalytic selective N-1 alkylation of benzotriazoles with diazoalkanes using 10 mol% of B(C6F5)(3), providing N-1-alkylated benzotriazoles in good to excellent yields. The protocol is successfully applied to gram-scale syntheses and a derivative with antimicrobial activity, showcasing its versatility and potential for practical applications.