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

Yunbo Zhao; Dipendu Mandal; Jing Guo; Yile Wu; Douglas W Stephan

doi:10.1039/d1cc03048e

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

Chem Commun (Camb). 2021 Aug 5;57(63):7758-7761. doi: 10.1039/d1cc03048e.

Authors

Yunbo Zhao¹, Dipendu Mandal¹, Jing Guo¹, Yile Wu¹, Douglas W Stephan²

Affiliations

¹ Institute of Drug Discovery Technology, Ningbo University, Zhejiang, China. guojing@nbu.edu.cn.
² Institute of Drug Discovery Technology, Ningbo University, Zhejiang, China. guojing@nbu.edu.cn and Department of Chemistry, University of Toronto, Toronto, 80 St. George Street, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.

PMID: 34254070
DOI: 10.1039/d1cc03048e

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.