Regioselective Synthesis of N2 -Alkylated-1,2,3 Triazoles and N1 -Alkylated Benzotriazoles: Cu2 S as a Recyclable Nanocatalyst for Oxidative Amination of N, N-Dimethylbenzylamines

The Journal of Organic Chemistry
Sonu GuptaNidhi Jain

Abstract

Copper chalcogenide nanoparticles (Cu2S) synthesized for the first time from a single-source precursor, CuSPh, act as highly efficient and reusable heterogeneous catalyst for regioselective amination of N, N-dimethylbenzylamines with various azoles. The reaction involves N-H/C-H cross-dehydrogenative coupling (CDC) and demonstrates wide functional group tolerance. It provides highly selective access to N1-alkylated benzotriazoles, N2-alkylated 1,2,3-triazoles and 4-phenyl-1,2,3-triazoles, and N-alkylated carbazoles in 70-89% yields under solvent-free conditions. The Cu2S nanocatalyst has been characterized by PXRD, XPS, SEM-EDX, and HR-TEM analysis. Mechanistic studies suggest that the reaction follows a radical pathway and involves an iminium ion intermediate.

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Citations

Aug 18, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Preeti OswalArun Kumar
Jul 19, 2020·Applied and Environmental Microbiology·Richard L KimberJonathan R Lloyd
Nov 11, 2021·Nanoscale·Marc CamatsMontserrat Gómez
Dec 8, 2021·The Journal of Organic Chemistry·Junbin ShiNing Liu

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