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Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes

The full control of positional selectivity is of prime importance in C–H activation technology. Chelation assistance served as the stimulus for the development of a plethora of ortho-selective arene functionalizations. In sharp contrast, meta-selective C–H functionalizations continue to be scarce, w...

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Autores principales: Li, Jie, Korvorapun, Korkit, De Sarkar, Suman, Rogge, Torben, Burns, David J., Warratz, Svenja, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5472771/
https://www.ncbi.nlm.nih.gov/pubmed/28598411
http://dx.doi.org/10.1038/ncomms15430
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author Li, Jie
Korvorapun, Korkit
De Sarkar, Suman
Rogge, Torben
Burns, David J.
Warratz, Svenja
Ackermann, Lutz
author_facet Li, Jie
Korvorapun, Korkit
De Sarkar, Suman
Rogge, Torben
Burns, David J.
Warratz, Svenja
Ackermann, Lutz
author_sort Li, Jie
collection PubMed
description The full control of positional selectivity is of prime importance in C–H activation technology. Chelation assistance served as the stimulus for the development of a plethora of ortho-selective arene functionalizations. In sharp contrast, meta-selective C–H functionalizations continue to be scarce, with all ruthenium-catalysed transformations currently requiring difficult to remove or modify nitrogen-containing heterocycles. Herein, we describe a unifying concept to access a wealth of meta-decorated arenes by a unique arene ligand effect in proximity-induced ruthenium(II) C–H activation catalysis. The transformative nature of our strategy is mirrored by providing a step-economical entry to a range of meta-substituted arenes, including ketones, acids, amines and phenols—key structural motifs in crop protection, material sciences, medicinal chemistry and pharmaceutical industries.
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spelling pubmed-54727712017-06-28 Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes Li, Jie Korvorapun, Korkit De Sarkar, Suman Rogge, Torben Burns, David J. Warratz, Svenja Ackermann, Lutz Nat Commun Article The full control of positional selectivity is of prime importance in C–H activation technology. Chelation assistance served as the stimulus for the development of a plethora of ortho-selective arene functionalizations. In sharp contrast, meta-selective C–H functionalizations continue to be scarce, with all ruthenium-catalysed transformations currently requiring difficult to remove or modify nitrogen-containing heterocycles. Herein, we describe a unifying concept to access a wealth of meta-decorated arenes by a unique arene ligand effect in proximity-induced ruthenium(II) C–H activation catalysis. The transformative nature of our strategy is mirrored by providing a step-economical entry to a range of meta-substituted arenes, including ketones, acids, amines and phenols—key structural motifs in crop protection, material sciences, medicinal chemistry and pharmaceutical industries. Nature Publishing Group 2017-06-09 /pmc/articles/PMC5472771/ /pubmed/28598411 http://dx.doi.org/10.1038/ncomms15430 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Li, Jie
Korvorapun, Korkit
De Sarkar, Suman
Rogge, Torben
Burns, David J.
Warratz, Svenja
Ackermann, Lutz
Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title_full Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title_fullStr Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title_full_unstemmed Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title_short Ruthenium(II)-catalysed remote C–H alkylations as a versatile platform to meta-decorated arenes
title_sort ruthenium(ii)-catalysed remote c–h alkylations as a versatile platform to meta-decorated arenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5472771/
https://www.ncbi.nlm.nih.gov/pubmed/28598411
http://dx.doi.org/10.1038/ncomms15430
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