Issue 11, 2021

Prolinamide plays a key role in promoting copper-catalyzed cycloaddition of azides and alkynes in aqueous media via unprecedented metallacycle intermediates

Abstract

We herein delineate cycloaddition of a wide range of azides with terminal alkynes using catalytic CuI and a prolinamide ligand in aqueous media under aerobic conditions. The catalytic system is used for a ‘one-pot’ synthesis of triazoles from aliphatic halides and alkynes. A detailed computational study predicts that prolinamide plays a unique role in facilitating the cycloaddition in water via the formation of remarkable metallacycle intermediates. The synthetic utility of the method is demonstrated by the synthesis of pharmacologically relevant triazolyl diaryl amines via a Cu(I) catalyzed relay cycloaddition and Ullmann coupling sequence.

Graphical abstract: Prolinamide plays a key role in promoting copper-catalyzed cycloaddition of azides and alkynes in aqueous media via unprecedented metallacycle intermediates

Supplementary files

Article information

Article type
Research Article
Submitted
20 9 2020
Accepted
15 3 2021
First published
17 3 2021

Org. Chem. Front., 2021,8, 2434-2441

Prolinamide plays a key role in promoting copper-catalyzed cycloaddition of azides and alkynes in aqueous media via unprecedented metallacycle intermediates

G. Chakraborti, R. Jana, T. Mandal, A. Datta and J. Dash, Org. Chem. Front., 2021, 8, 2434 DOI: 10.1039/D0QO01150A

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