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The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst

A four-component green tandem approach for the metal-free synthesis of polyfunctionalized dihydro-2-oxypyrroles was devised using the Michael–Mannich cyclocondensation of amines, dialkyl acetylenedicarboxylaes, and formaldehyde. Photo-excited state functions generated from methylene blue (MB(+)) wer...

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Autor principal: Mohamadpour, Farzaneh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8984404/
https://www.ncbi.nlm.nih.gov/pubmed/35425003
http://dx.doi.org/10.1039/d2ra01190e
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author Mohamadpour, Farzaneh
author_facet Mohamadpour, Farzaneh
author_sort Mohamadpour, Farzaneh
collection PubMed
description A four-component green tandem approach for the metal-free synthesis of polyfunctionalized dihydro-2-oxypyrroles was devised using the Michael–Mannich cyclocondensation of amines, dialkyl acetylenedicarboxylaes, and formaldehyde. Photo-excited state functions generated from methylene blue (MB(+)) were employed as single-electron transfer (SET) and energy transfer (EnT) catalysts at ambient temperature in an ethanol solvent, employing visible light as a renewable energy source in the air atmosphere. This study aims to increase the usage of a non-metal cationic dye that is both inexpensive and widely available. Methylene blue is photochemically produced with the least amount of a catalyst due to its high yields, energy-effectiveness, high atom economy, time-saving features of the reaction, and operational simplicity. As a result, a variety of ecological and long-term chemical features are achieved. Surprisingly, such cyclization can be done on a gram scale, implying that the process has industrial potential.
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spelling pubmed-89844042022-04-13 The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst Mohamadpour, Farzaneh RSC Adv Chemistry A four-component green tandem approach for the metal-free synthesis of polyfunctionalized dihydro-2-oxypyrroles was devised using the Michael–Mannich cyclocondensation of amines, dialkyl acetylenedicarboxylaes, and formaldehyde. Photo-excited state functions generated from methylene blue (MB(+)) were employed as single-electron transfer (SET) and energy transfer (EnT) catalysts at ambient temperature in an ethanol solvent, employing visible light as a renewable energy source in the air atmosphere. This study aims to increase the usage of a non-metal cationic dye that is both inexpensive and widely available. Methylene blue is photochemically produced with the least amount of a catalyst due to its high yields, energy-effectiveness, high atom economy, time-saving features of the reaction, and operational simplicity. As a result, a variety of ecological and long-term chemical features are achieved. Surprisingly, such cyclization can be done on a gram scale, implying that the process has industrial potential. The Royal Society of Chemistry 2022-04-06 /pmc/articles/PMC8984404/ /pubmed/35425003 http://dx.doi.org/10.1039/d2ra01190e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Mohamadpour, Farzaneh
The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title_full The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title_fullStr The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title_full_unstemmed The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title_short The development of imin-based tandem Michael–Mannich cyclocondensation through a single-electron transfer (SET)/energy transfer (EnT) pathway in the use of methylene blue (MB(+)) as a photo-redox catalyst
title_sort development of imin-based tandem michael–mannich cyclocondensation through a single-electron transfer (set)/energy transfer (ent) pathway in the use of methylene blue (mb(+)) as a photo-redox catalyst
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8984404/
https://www.ncbi.nlm.nih.gov/pubmed/35425003
http://dx.doi.org/10.1039/d2ra01190e
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