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
28 شوال 1442
Accepted
26 ذو القعدة 1442
First published
26 ذو القعدة 1442

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements