Issue 30, 2022

Mechanistic investigation of enolate/stabilized vinylogous carbanion-mediated organocatalytic azide (3 + 2) cycloaddition reactions for the synthesis of 1,2,3-triazoles

Abstract

Herein, we report a fully detailed mechanistic study involving an organocatalyzed 1,3-dipolar cycloaddition via enolate or stabilized vinylogous carbanion intermediates and azide for the synthesis of 1,2,3-triazoles. A detailed investigation of the elementary steps, intermediates, and transition states of the two organocatalyzed metal-free click reactions is supported by DFT calculations and 1H NMR monitoring experiments, providing detailed profiles for both reaction mechanisms. Distortion–interaction activation-strain (DIAS) analysis was also employed to further elucidate the regioselectivity in both reactions.

Graphical abstract: Mechanistic investigation of enolate/stabilized vinylogous carbanion-mediated organocatalytic azide (3 + 2) cycloaddition reactions for the synthesis of 1,2,3-triazoles

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
24 2 2022
Accepted
29 3 2022
First published
30 3 2022

Org. Biomol. Chem., 2022,20, 6019-6026

Mechanistic investigation of enolate/stabilized vinylogous carbanion-mediated organocatalytic azide (3 + 2) cycloaddition reactions for the synthesis of 1,2,3-triazoles

A. Chiavegatti Neto, K. C. Soares, M. D. S. Santos, T. J. Aímola, A. G. Ferreira, G. A. M. Jardim, C. F. Tormena, M. W. Paixão and M. A. B. Ferreira, Org. Biomol. Chem., 2022, 20, 6019 DOI: 10.1039/D2OB00391K

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