Issue 16, 2024

A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles

Abstract

2,5-Dihydropyrrole derivatives are considered privileged structures as reflected by their presence in many biologically active molecules and therapeutic agents. Herein, we develop a concise and efficient method utilizing a commercially available copper salt as a catalyst to facilitate the formation of 2,5-dihydropyrroles from propargyl amines and diazo esters. This reaction proceeds via the formation of an N-ylide, followed by bond cleavage/recombination. Control experiments and density functional theory (DFT) calculations provide a detailed analysis of the reaction pathway. The key features of this protocol include simple operation, readily available starting materials, mild conditions, and high atom economy. In addition, the gram-scale preparation experiment and the transformations of 2,5-dihydropyrroles demonstrate the potential applicability of our synthetic method.

Graphical abstract: A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles

Supplementary files

Article information

Article type
Research Article
Submitted
25 Apr 2024
Accepted
23 Jun 2024
First published
26 Jun 2024

Org. Chem. Front., 2024,11, 4546-4555

A copper-catalyzed annulation reaction of diazo esters with propargyl amines for the synthesis of 2,5-dihydropyrroles

H. Xie, W. Zhao, H. Wei, Y. Yu, L. Zhao, J. B. Baell and F. Huang, Org. Chem. Front., 2024, 11, 4546 DOI: 10.1039/D4QO00751D

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