Alkyne‐Dependent Synthesis of Pyrrolines and Propargylamines through Metal‐Free Decarboxylation

Pyrrolines are crucial in the discovery and development of pharmaceuticals. Herein, a metal‐free multicomponent decarboxylative reaction has been developed that is extremely effective and brief. The reaction is performed to form iminium salt intermediates through decarboxylative condensation of N ‐benzylglycines and formaldehyde. Subsequent chemoselective [3 + 2] cyclization or nucleophilic addition of alkynes leads to the generation of various pyrrolines or propargylamines in moderate to good yields, respectively. The approach is environmentally benign, easily implemented, and tolerates a wide range of functional groups.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-07-13
DOI
https://doi.org/10.1002/ejoc.202500262
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Alkyne‐Dependent Synthesis of Pyrrolines and Propargylamines through Metal‐Free Decarboxylation

Ziqi Yi, Song Fan, Junhai Huang, Huangdi Feng et al.
European Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
article

Alkyne‐Dependent Synthesis of Pyrrolines and Propargylamines through Metal‐Free Decarboxylation

Ziqi Yi, Song Fan, Junhai Huang, Huangdi Feng, Peng Li
article en

Abstract

Pyrrolines are crucial in the discovery and development of pharmaceuticals. Herein, a metal‐free multicomponent decarboxylative reaction has been developed that is extremely effective and brief. The reaction is performed to form iminium salt intermediates through decarboxylative condensation of N ‐benzylglycines and formaldehyde. Subsequent chemoselective [3 + 2] cyclization or nucleophilic addition of alkynes leads to the generation of various pyrrolines or propargylamines in moderate to good yields, respectively. The approach is environmentally benign, easily implemented, and tolerates a wide range of functional groups.

European Journal of Organic ChemistryVol. 28(28)
Shanghai University of Engineering Science (CN)
National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality
Openalex Percentile: Top 87%
Asymmetric Synthesis and Catalysis
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