Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 63, Pages 7758-7761Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc03048e
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Funding
- Ningbo University [421999362, 422110973]
- Guggenheim Foundation
- Killam foundation
- Scientific Research Grant of Ningbo University [215-432000282]
- Ningbo Top Talent Project [215-432094250]
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The study demonstrates a metal-free catalytic selective N-1 alkylation of benzotriazoles with diazoalkanes using 10 mol% of B(C6F5)(3), providing N-1-alkylated benzotriazoles in good to excellent yields. The protocol is successfully applied to gram-scale syntheses and a derivative with antimicrobial activity, showcasing its versatility and potential for practical applications.
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(C6F5)(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.
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