Issue 64, 2021
From the journal:

Chemical Communications

A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water†

Gargi Chakraborti,‡a   Tirtha Mandal,‡a   Charles Patriot Roya  and  Jyotirmayee Dash ORCID logo *a  

* Corresponding authors

a School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032, India
E-mail: ocjd@iacs.res.in

Abstract

A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazoles via the regioselective formation of N2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI–prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resulting N2-carboxyalkylated triazoles.

Graphical abstract: A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water

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Article information

DOI
https://doi.org/10.1039/D1CC02801D
Article type
Communication
Submitted
27 May 2021
Accepted
13 Jul 2021
First published
13 Jul 2021

Chem. Commun., 2021,57, 7970-7973

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A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water

G. Chakraborti, T. Mandal, C. P. Roy and J. Dash, Chem. Commun., 2021, 57, 7970 DOI: 10.1039/D1CC02801D

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