Issue 63, 2021

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
09 Jūn. 2021
Accepted
06 Jūl. 2021
First published
06 Jūl. 2021

Chem. Commun., 2021,57, 7758-7761

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

Y. Zhao, D. Mandal, J. Guo, Y. Wu and D. W. Stephan, Chem. Commun., 2021, 57, 7758 DOI: 10.1039/D1CC03048E

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