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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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.
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Language:English
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container_issue 63
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container_title Chemical communications (Cambridge, England)
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creator Zhao, Yunbo
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description 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.
doi_str_mv 10.1039/D1CC03048E
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title B(C 6 F 5 ) 3 -Catalyzed site-selective N 1 -alkylation of benzotriazoles with diazoalkanes
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