Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination

Manganese‐catalyzed C−H bond activation chemistry is emerging as a powerful and complementary method for molecular functionalization. A highly reactive seven‐membered Mn(I) intermediate is detected and characterized that is effective for H‐transfer or reductive elimination to deliver alkenylated or...

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Autores principales: Yahaya, Nasiru P., Appleby, Kate M., Teh, Magdalene, Wagner, Conrad, Troschke, Erik, Bray, Joshua T. W., Duckett, Simon B., Hammarback, L. Anders, Ward, Jonathan S., Milani, Jessica, Pridmore, Natalie E., Whitwood, Adrian C., Lynam, Jason M., Fairlamb, Ian J. S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113680/
https://www.ncbi.nlm.nih.gov/pubmed/27603008
http://dx.doi.org/10.1002/anie.201606236
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author Yahaya, Nasiru P.
Appleby, Kate M.
Teh, Magdalene
Wagner, Conrad
Troschke, Erik
Bray, Joshua T. W.
Duckett, Simon B.
Hammarback, L. Anders
Ward, Jonathan S.
Milani, Jessica
Pridmore, Natalie E.
Whitwood, Adrian C.
Lynam, Jason M.
Fairlamb, Ian J. S.
author_facet Yahaya, Nasiru P.
Appleby, Kate M.
Teh, Magdalene
Wagner, Conrad
Troschke, Erik
Bray, Joshua T. W.
Duckett, Simon B.
Hammarback, L. Anders
Ward, Jonathan S.
Milani, Jessica
Pridmore, Natalie E.
Whitwood, Adrian C.
Lynam, Jason M.
Fairlamb, Ian J. S.
author_sort Yahaya, Nasiru P.
collection PubMed
description Manganese‐catalyzed C−H bond activation chemistry is emerging as a powerful and complementary method for molecular functionalization. A highly reactive seven‐membered Mn(I) intermediate is detected and characterized that is effective for H‐transfer or reductive elimination to deliver alkenylated or pyridinium products, respectively. The two pathways are determined at Mn(I) by judicious choice of an electron‐deficient 2‐pyrone substrate containing a 2‐pyridyl directing group, which undergoes regioselective C−H bond activation, serving as a valuable system for probing the mechanistic features of Mn C−H bond activation chemistry.
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spelling pubmed-51136802016-12-02 Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination Yahaya, Nasiru P. Appleby, Kate M. Teh, Magdalene Wagner, Conrad Troschke, Erik Bray, Joshua T. W. Duckett, Simon B. Hammarback, L. Anders Ward, Jonathan S. Milani, Jessica Pridmore, Natalie E. Whitwood, Adrian C. Lynam, Jason M. Fairlamb, Ian J. S. Angew Chem Int Ed Engl Communications Manganese‐catalyzed C−H bond activation chemistry is emerging as a powerful and complementary method for molecular functionalization. A highly reactive seven‐membered Mn(I) intermediate is detected and characterized that is effective for H‐transfer or reductive elimination to deliver alkenylated or pyridinium products, respectively. The two pathways are determined at Mn(I) by judicious choice of an electron‐deficient 2‐pyrone substrate containing a 2‐pyridyl directing group, which undergoes regioselective C−H bond activation, serving as a valuable system for probing the mechanistic features of Mn C−H bond activation chemistry. John Wiley and Sons Inc. 2016-09-07 2016-09-26 /pmc/articles/PMC5113680/ /pubmed/27603008 http://dx.doi.org/10.1002/anie.201606236 Text en © 2016 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 Communications
Yahaya, Nasiru P.
Appleby, Kate M.
Teh, Magdalene
Wagner, Conrad
Troschke, Erik
Bray, Joshua T. W.
Duckett, Simon B.
Hammarback, L. Anders
Ward, Jonathan S.
Milani, Jessica
Pridmore, Natalie E.
Whitwood, Adrian C.
Lynam, Jason M.
Fairlamb, Ian J. S.
Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title_full Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title_fullStr Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title_full_unstemmed Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title_short Manganese(I)‐Catalyzed C−H Activation: The Key Role of a 7‐Membered Manganacycle in H‐Transfer and Reductive Elimination
title_sort manganese(i)‐catalyzed c−h activation: the key role of a 7‐membered manganacycle in h‐transfer and reductive elimination
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113680/
https://www.ncbi.nlm.nih.gov/pubmed/27603008
http://dx.doi.org/10.1002/anie.201606236
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