Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes

We report herein the development of a palladium-catalyzed, multicomponent synthesis of indolizines. The reaction proceeds via the carbonylative formation of a high energy, mesoionic pyridine-based 1,3-dipole, which can undergo spontaneous cycloaddition with alkynes. Overall, this provides a route to...

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Autores principales: Roy, Sébastien A., Zgheib, José, Zhou, Cuihan, Arndtsen, Bruce A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179343/
https://www.ncbi.nlm.nih.gov/pubmed/34163991
http://dx.doi.org/10.1039/d0sc03977b
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author Roy, Sébastien A.
Zgheib, José
Zhou, Cuihan
Arndtsen, Bruce A.
author_facet Roy, Sébastien A.
Zgheib, José
Zhou, Cuihan
Arndtsen, Bruce A.
author_sort Roy, Sébastien A.
collection PubMed
description We report herein the development of a palladium-catalyzed, multicomponent synthesis of indolizines. The reaction proceeds via the carbonylative formation of a high energy, mesoionic pyridine-based 1,3-dipole, which can undergo spontaneous cycloaddition with alkynes. Overall, this provides a route to prepare indolizines in a modular fashion from combinations of commercially available or easily generated reagents: 2-bromopyridines, imines and alkynes.
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spelling pubmed-81793432021-06-22 Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes Roy, Sébastien A. Zgheib, José Zhou, Cuihan Arndtsen, Bruce A. Chem Sci Chemistry We report herein the development of a palladium-catalyzed, multicomponent synthesis of indolizines. The reaction proceeds via the carbonylative formation of a high energy, mesoionic pyridine-based 1,3-dipole, which can undergo spontaneous cycloaddition with alkynes. Overall, this provides a route to prepare indolizines in a modular fashion from combinations of commercially available or easily generated reagents: 2-bromopyridines, imines and alkynes. The Royal Society of Chemistry 2020-12-22 /pmc/articles/PMC8179343/ /pubmed/34163991 http://dx.doi.org/10.1039/d0sc03977b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Roy, Sébastien A.
Zgheib, José
Zhou, Cuihan
Arndtsen, Bruce A.
Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title_full Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title_fullStr Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title_full_unstemmed Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title_short Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
title_sort palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179343/
https://www.ncbi.nlm.nih.gov/pubmed/34163991
http://dx.doi.org/10.1039/d0sc03977b
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