Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality

Thioethers allowed for highly atroposelective C–H olefinations by a palladium/chiral phosphoric acid catalytic system under ambient air. Both N–C and C–C axial chiral (hetero)biaryls were successfully constructed, leading to a broad range of axially chiral N-aryl indoles and biaryls with excellent e...

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Detalles Bibliográficos
Autores principales: Li, Yanjun, Liou, Yan-Cheng, Chen, Xinran, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985512/
https://www.ncbi.nlm.nih.gov/pubmed/35440980
http://dx.doi.org/10.1039/d2sc00748g
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author Li, Yanjun
Liou, Yan-Cheng
Chen, Xinran
Ackermann, Lutz
author_facet Li, Yanjun
Liou, Yan-Cheng
Chen, Xinran
Ackermann, Lutz
author_sort Li, Yanjun
collection PubMed
description Thioethers allowed for highly atroposelective C–H olefinations by a palladium/chiral phosphoric acid catalytic system under ambient air. Both N–C and C–C axial chiral (hetero)biaryls were successfully constructed, leading to a broad range of axially chiral N-aryl indoles and biaryls with excellent enantioselectivities up to 99% ee. Experimental and computational studies were conducted to unravel the walking mode for the atroposelective C–H olefination. A plausible chiral induction model for the enantioselectivity-determining step was established by detailed DFT calculations.
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spelling pubmed-89855122022-04-18 Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality Li, Yanjun Liou, Yan-Cheng Chen, Xinran Ackermann, Lutz Chem Sci Chemistry Thioethers allowed for highly atroposelective C–H olefinations by a palladium/chiral phosphoric acid catalytic system under ambient air. Both N–C and C–C axial chiral (hetero)biaryls were successfully constructed, leading to a broad range of axially chiral N-aryl indoles and biaryls with excellent enantioselectivities up to 99% ee. Experimental and computational studies were conducted to unravel the walking mode for the atroposelective C–H olefination. A plausible chiral induction model for the enantioselectivity-determining step was established by detailed DFT calculations. The Royal Society of Chemistry 2022-03-10 /pmc/articles/PMC8985512/ /pubmed/35440980 http://dx.doi.org/10.1039/d2sc00748g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Li, Yanjun
Liou, Yan-Cheng
Chen, Xinran
Ackermann, Lutz
Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title_full Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title_fullStr Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title_full_unstemmed Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title_short Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality
title_sort thioether-enabled palladium-catalyzed atroposelective c–h olefination for n–c and c–c axial chirality
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8985512/
https://www.ncbi.nlm.nih.gov/pubmed/35440980
http://dx.doi.org/10.1039/d2sc00748g
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AT chenxinran thioetherenabledpalladiumcatalyzedatroposelectivecholefinationforncandccaxialchirality
AT ackermannlutz thioetherenabledpalladiumcatalyzedatroposelectivecholefinationforncandccaxialchirality

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