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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
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The Royal Society of Chemistry
2022
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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. |
format | Online Article Text |
id | pubmed-8984404 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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