Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity

(Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented post...

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Autores principales: Demory, Emilien, Devaraj, Karthik, Orthaber, Andreas, Gates, Paul J, Pilarski, Lukasz T
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4600243/
https://www.ncbi.nlm.nih.gov/pubmed/26270451
http://dx.doi.org/10.1002/anie.201503152
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author Demory, Emilien
Devaraj, Karthik
Orthaber, Andreas
Gates, Paul J
Pilarski, Lukasz T
author_facet Demory, Emilien
Devaraj, Karthik
Orthaber, Andreas
Gates, Paul J
Pilarski, Lukasz T
author_sort Demory, Emilien
collection PubMed
description (Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride-activated (hetero)aryne precursors, for example, as substrates in transition-metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.
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spelling pubmed-46002432015-10-14 Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity Demory, Emilien Devaraj, Karthik Orthaber, Andreas Gates, Paul J Pilarski, Lukasz T Angew Chem Int Ed Engl Communications (Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride-activated (hetero)aryne precursors, for example, as substrates in transition-metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups. WILEY-VCH Verlag 2015-09-28 2015-08-13 /pmc/articles/PMC4600243/ /pubmed/26270451 http://dx.doi.org/10.1002/anie.201503152 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. https://creativecommons.org/licenses/by-nc-nd/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Communications
Demory, Emilien
Devaraj, Karthik
Orthaber, Andreas
Gates, Paul J
Pilarski, Lukasz T
Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title_full Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title_fullStr Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title_full_unstemmed Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title_short Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C–H Activation and Orthogonal Reactivity
title_sort boryl (hetero)aryne precursors as versatile arylation reagents: synthesis through c–h activation and orthogonal reactivity
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4600243/
https://www.ncbi.nlm.nih.gov/pubmed/26270451
http://dx.doi.org/10.1002/anie.201503152
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