B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed site-selective <i>N</i><sup>1</sup>-alkylation of benzotriazoles with diazoalkanes
Yunbo Zhao, Dipendu Mandal, Jing Guo, Yile Wu, Douglas W. Stephan
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.
Topics & Concepts
AlkylationCatalysisChemistryMedicinal chemistryOrganic chemistryOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions