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

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Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of… Click to show full abstract

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-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.

Keywords: alkylation benzotriazoles; site selective; selective alkylation; benzotriazoles diazoalkanes; alkylation

Journal Title: Chemical communications
Year Published: 2021

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