Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones

A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one‐pot procedure: dehydrogenation of 2,2‐disubstituted cyclopentane‐1,3‐diones and the subsequent oxidative Heck coupling. This auto‐tandem catalytic reaction is applicable to both batch and...

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Autores principales: Lamb, Claire J. C., Nderitu, Bryan G., McMurdo, Gemma, Tobin, John M., Vilela, Filipe, Lee, Ai‐Lan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767738/
https://www.ncbi.nlm.nih.gov/pubmed/29105890
http://dx.doi.org/10.1002/chem.201704442
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author Lamb, Claire J. C.
Nderitu, Bryan G.
McMurdo, Gemma
Tobin, John M.
Vilela, Filipe
Lee, Ai‐Lan
author_facet Lamb, Claire J. C.
Nderitu, Bryan G.
McMurdo, Gemma
Tobin, John M.
Vilela, Filipe
Lee, Ai‐Lan
author_sort Lamb, Claire J. C.
collection PubMed
description A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one‐pot procedure: dehydrogenation of 2,2‐disubstituted cyclopentane‐1,3‐diones and the subsequent oxidative Heck coupling. This auto‐tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrisation of the all‐C quaternary centre was successfully achieved.
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spelling pubmed-57677382018-02-01 Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones Lamb, Claire J. C. Nderitu, Bryan G. McMurdo, Gemma Tobin, John M. Vilela, Filipe Lee, Ai‐Lan Chemistry Full Papers A Pd(II) catalyst system has been used to successfully catalyse two mechanistically distinct reactions in a one‐pot procedure: dehydrogenation of 2,2‐disubstituted cyclopentane‐1,3‐diones and the subsequent oxidative Heck coupling. This auto‐tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrisation of the all‐C quaternary centre was successfully achieved. John Wiley and Sons Inc. 2017-11-30 2017-12-22 /pmc/articles/PMC5767738/ /pubmed/29105890 http://dx.doi.org/10.1002/chem.201704442 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Lamb, Claire J. C.
Nderitu, Bryan G.
McMurdo, Gemma
Tobin, John M.
Vilela, Filipe
Lee, Ai‐Lan
Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title_full Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title_fullStr Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title_full_unstemmed Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title_short Auto‐Tandem Catalysis: Pd(II)‐Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane‐1,3‐diones
title_sort auto‐tandem catalysis: pd(ii)‐catalysed dehydrogenation/oxidative heck reaction of cyclopentane‐1,3‐diones
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5767738/
https://www.ncbi.nlm.nih.gov/pubmed/29105890
http://dx.doi.org/10.1002/chem.201704442
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