B(C 6 F 5 ) 3 -Catalyzed site-selective N 1 -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(C 6 F 5 ) 3 . These reactions provide N 1 -alky...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-08, Vol.57 (63), p.7758-7761
Main Authors: Zhao, Yunbo, Mandal, Dipendu, Guo, Jing, Wu, Yile, Stephan, Douglas W.
Format: Article
Language:English
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Summary: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(C 6 F 5 ) 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/D1CC03048E