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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...

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Autores principales: Fan, Xinyuan, Gong, Xu, Ma, Mengyue, Wang, Rui, Walsh, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
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.
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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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