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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...

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Autores principales: Chen, Qiao, Zhu, Tingshun, Majhi, Pankaj Kumar, Mou, Chengli, Chai, Huifang, Zhang, Jingjie, Zhuo, Shitian, Chi, Yonggui Robin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
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.
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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
title_full Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
title_fullStr Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
title_full_unstemmed Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
title_short Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
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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