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Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids
Light-mediated transformations with CO(2) have recently attracted great attention, with the focus on CO(2) incorporation into C–C double and triple bonds, organohalides and amines. Herein is demonstrated visible light -mediated umpolung imine reactivity capable of engaging CO(2) to afford α-amino ac...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6250672/ https://www.ncbi.nlm.nih.gov/pubmed/30467333 http://dx.doi.org/10.1038/s41467-018-07351-2 |
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author | Fan, Xinyuan Gong, Xu Ma, Mengyue Wang, Rui Walsh, Patrick J. |
author_facet | Fan, Xinyuan Gong, Xu Ma, Mengyue Wang, Rui Walsh, Patrick J. |
author_sort | Fan, Xinyuan |
collection | PubMed |
description | Light-mediated transformations with CO(2) have recently attracted great attention, with the focus on CO(2) incorporation into C–C double and triple bonds, organohalides and amines. Herein is demonstrated visible light -mediated umpolung imine reactivity capable of engaging CO(2) to afford α-amino acid derivatives. By employing benzophenone ketimine derivatives, CO(2) fixation by hydrocarboxylation of C=N double bonds is achieved. Good to excellent yields of a broad range of α,α–disubstituted α-amino acid derivatives are obtained under mild conditions (rt, atmospheric pressure of CO(2), visible light). A procedure that avoids tedious chromatographic purification and uses sustainable sunlight is developed to highlight the simplicity of this method. |
format | Online Article Text |
id | pubmed-6250672 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-62506722018-11-26 Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids Fan, Xinyuan Gong, Xu Ma, Mengyue Wang, Rui Walsh, Patrick J. Nat Commun Article Light-mediated transformations with CO(2) have recently attracted great attention, with the focus on CO(2) incorporation into C–C double and triple bonds, organohalides and amines. Herein is demonstrated visible light -mediated umpolung imine reactivity capable of engaging CO(2) to afford α-amino acid derivatives. By employing benzophenone ketimine derivatives, CO(2) fixation by hydrocarboxylation of C=N double bonds is achieved. Good to excellent yields of a broad range of α,α–disubstituted α-amino acid derivatives are obtained under mild conditions (rt, atmospheric pressure of CO(2), visible light). A procedure that avoids tedious chromatographic purification and uses sustainable sunlight is developed to highlight the simplicity of this method. Nature Publishing Group UK 2018-11-22 /pmc/articles/PMC6250672/ /pubmed/30467333 http://dx.doi.org/10.1038/s41467-018-07351-2 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Fan, Xinyuan Gong, Xu Ma, Mengyue Wang, Rui Walsh, Patrick J. Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title | Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title_full | Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title_fullStr | Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title_full_unstemmed | Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title_short | Visible light-promoted CO(2) fixation with imines to synthesize diaryl α-amino acids |
title_sort | visible light-promoted co(2) fixation with imines to synthesize diaryl α-amino acids |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6250672/ https://www.ncbi.nlm.nih.gov/pubmed/30467333 http://dx.doi.org/10.1038/s41467-018-07351-2 |
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