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Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon–hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon–hydro...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263396/ https://www.ncbi.nlm.nih.gov/pubmed/30595836 http://dx.doi.org/10.1039/c8sc03480j |
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author | Chen, Qiao Zhu, Tingshun Majhi, Pankaj Kumar Mou, Chengli Chai, Huifang Zhang, Jingjie Zhuo, Shitian Chi, Yonggui Robin |
author_facet | Chen, Qiao Zhu, Tingshun Majhi, Pankaj Kumar Mou, Chengli Chai, Huifang Zhang, Jingjie Zhuo, Shitian Chi, Yonggui Robin |
author_sort | Chen, Qiao |
collection | PubMed |
description | Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon–hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon–hydrogen bond and the difficult enantiofacial discrimination of two sterically similar aryl substituents. Here we disclose an N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes. Our method allows for highly enantioselective transformation of diaryl methanes and quick access to benzimidazole fused lactams. |
format | Online Article Text |
id | pubmed-6263396 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-62633962018-12-28 Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes Chen, Qiao Zhu, Tingshun Majhi, Pankaj Kumar Mou, Chengli Chai, Huifang Zhang, Jingjie Zhuo, Shitian Chi, Yonggui Robin Chem Sci Chemistry Di(hetero)arylmethane is a unique structural motif for natural and synthetic functional molecules. To date, it remains challenging to functionalize the diaryl methyl sp3 carbon–hydrogen bond directly in an enantioselective manner. This is likely due to the relatively inert nature of the carbon–hydrogen bond and the difficult enantiofacial discrimination of two sterically similar aryl substituents. Here we disclose an N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes. Our method allows for highly enantioselective transformation of diaryl methanes and quick access to benzimidazole fused lactams. Royal Society of Chemistry 2018-09-18 /pmc/articles/PMC6263396/ /pubmed/30595836 http://dx.doi.org/10.1039/c8sc03480j Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Chen, Qiao Zhu, Tingshun Majhi, Pankaj Kumar Mou, Chengli Chai, Huifang Zhang, Jingjie Zhuo, Shitian Chi, Yonggui Robin Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes |
title | Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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title_full | Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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title_fullStr | Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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title_full_unstemmed | Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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title_short | Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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title_sort | carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263396/ https://www.ncbi.nlm.nih.gov/pubmed/30595836 http://dx.doi.org/10.1039/c8sc03480j |
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