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Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry
The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a proto...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9847662/ https://www.ncbi.nlm.nih.gov/pubmed/36741520 http://dx.doi.org/10.1039/d2sc05428k |
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author | Yuan, Yin Yang, Junfeng Zhang, Junliang |
author_facet | Yuan, Yin Yang, Junfeng Zhang, Junliang |
author_sort | Yuan, Yin |
collection | PubMed |
description | The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a protocol for Cu-catalyzed enantioselective decarboxylative cyanation via the merger of photocatalysis and electrochemistry. CeCl(3) and Cu/BOX were used as co-catalysts to promote the decarboxylation and cyanation, and both catalysts were regenerated via anodic oxidation. This method establishes a proof of concept enantioselective transformation via photoelectrocatalysis. Studies by DFT calculations provided mechanistic insight on enantioselectivity control. |
format | Online Article Text |
id | pubmed-9847662 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-98476622023-02-03 Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry Yuan, Yin Yang, Junfeng Zhang, Junliang Chem Sci Chemistry The development of an efficient and straightforward method for decarboxylative coupling using common alkyl carboxylic acid is of great value. However, decarboxylative coupling with nucleophiles always needs stoichiometric chemical oxidants or substrate prefunctionalization. Herein, we report a protocol for Cu-catalyzed enantioselective decarboxylative cyanation via the merger of photocatalysis and electrochemistry. CeCl(3) and Cu/BOX were used as co-catalysts to promote the decarboxylation and cyanation, and both catalysts were regenerated via anodic oxidation. This method establishes a proof of concept enantioselective transformation via photoelectrocatalysis. Studies by DFT calculations provided mechanistic insight on enantioselectivity control. The Royal Society of Chemistry 2022-12-07 /pmc/articles/PMC9847662/ /pubmed/36741520 http://dx.doi.org/10.1039/d2sc05428k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yuan, Yin Yang, Junfeng Zhang, Junliang Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title | Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title_full | Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title_fullStr | Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title_full_unstemmed | Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title_short | Cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
title_sort | cu-catalyzed enantioselective decarboxylative cyanation via the synergistic merger of photocatalysis and electrochemistry |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9847662/ https://www.ncbi.nlm.nih.gov/pubmed/36741520 http://dx.doi.org/10.1039/d2sc05428k |
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