Cargando…

Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines

[Image: see text] Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized microcrystalline cellulose. A solvent-controlled chemoselectivity of the reaction was observed, leading to the chemodivergent...

Descripción completa

Detalles Bibliográficos
Autores principales: Zheng, Zhiyao, Deiana, Luca, Posevins, Daniels, Rafi, Abdolrahim A., Zhang, Kaiheng, Johansson, Magnus J., Tai, Cheuk-Wai, Córdova, Armando, Bäckvall, Jan-E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8822631/
https://www.ncbi.nlm.nih.gov/pubmed/35154848
http://dx.doi.org/10.1021/acscatal.1c05147
_version_ 1784646634572873728
author Zheng, Zhiyao
Deiana, Luca
Posevins, Daniels
Rafi, Abdolrahim A.
Zhang, Kaiheng
Johansson, Magnus J.
Tai, Cheuk-Wai
Córdova, Armando
Bäckvall, Jan-E.
author_facet Zheng, Zhiyao
Deiana, Luca
Posevins, Daniels
Rafi, Abdolrahim A.
Zhang, Kaiheng
Johansson, Magnus J.
Tai, Cheuk-Wai
Córdova, Armando
Bäckvall, Jan-E.
author_sort Zheng, Zhiyao
collection PubMed
description [Image: see text] Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized microcrystalline cellulose. A solvent-controlled chemoselectivity of the reaction was observed, leading to the chemodivergent synthesis of pyrrolines (2,5-dihydropyrroles) and pyrroles. The heterogeneous copper catalyst exhibits high efficiency and good recyclability in the Alder-ene reaction, constituting a highly attractive catalytic system from an economical and environmental point of view.
format Online
Article
Text
id pubmed-8822631
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-88226312022-02-09 Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines Zheng, Zhiyao Deiana, Luca Posevins, Daniels Rafi, Abdolrahim A. Zhang, Kaiheng Johansson, Magnus J. Tai, Cheuk-Wai Córdova, Armando Bäckvall, Jan-E. ACS Catal [Image: see text] Herein, we describe an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides. The copper nanoparticles were immobilized on amino-functionalized microcrystalline cellulose. A solvent-controlled chemoselectivity of the reaction was observed, leading to the chemodivergent synthesis of pyrrolines (2,5-dihydropyrroles) and pyrroles. The heterogeneous copper catalyst exhibits high efficiency and good recyclability in the Alder-ene reaction, constituting a highly attractive catalytic system from an economical and environmental point of view. American Chemical Society 2022-01-18 2022-02-04 /pmc/articles/PMC8822631/ /pubmed/35154848 http://dx.doi.org/10.1021/acscatal.1c05147 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Zheng, Zhiyao
Deiana, Luca
Posevins, Daniels
Rafi, Abdolrahim A.
Zhang, Kaiheng
Johansson, Magnus J.
Tai, Cheuk-Wai
Córdova, Armando
Bäckvall, Jan-E.
Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title_full Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title_fullStr Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title_full_unstemmed Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title_short Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines
title_sort efficient heterogeneous copper-catalyzed alder-ene reaction of allenynamides to pyrrolines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8822631/
https://www.ncbi.nlm.nih.gov/pubmed/35154848
http://dx.doi.org/10.1021/acscatal.1c05147
work_keys_str_mv AT zhengzhiyao efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT deianaluca efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT posevinsdaniels efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT rafiabdolrahima efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT zhangkaiheng efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT johanssonmagnusj efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT taicheukwai efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT cordovaarmando efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines
AT backvalljane efficientheterogeneouscoppercatalyzedalderenereactionofallenynamidestopyrrolines