Cargando…
Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones**
Three orthogonal cascade C—H functionalization processes are described, based on ruthenium-catalyzed C—H alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl(2)}(...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
WILEY-VCH Verlag
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4265981/ https://www.ncbi.nlm.nih.gov/pubmed/24453063 http://dx.doi.org/10.1002/anie.201309114 |
_version_ | 1782348957364518912 |
---|---|
author | Mehta, Vaibhav P García-López, José-Antonio Greaney, Michael F |
author_facet | Mehta, Vaibhav P García-López, José-Antonio Greaney, Michael F |
author_sort | Mehta, Vaibhav P |
collection | PubMed |
description | Three orthogonal cascade C—H functionalization processes are described, based on ruthenium-catalyzed C—H alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl(2)}(2)] and stoichiometric Cu(OAc)(2). Each transformation uses C—H functionalization methods to form C—C bonds sequentially, with the indeno furanone synthesis featuring a C—O bond formation as the terminating step. This work demonstrates the power of ruthenium-catalyzed alkenylation as a platform reaction to develop more complex transformations, with multiple C—H functionalization steps taking place in a single operation to access novel carbocyclic structures. |
format | Online Article Text |
id | pubmed-4265981 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | WILEY-VCH Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-42659812014-12-30 Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** Mehta, Vaibhav P García-López, José-Antonio Greaney, Michael F Angew Chem Int Ed Engl Communications Three orthogonal cascade C—H functionalization processes are described, based on ruthenium-catalyzed C—H alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl(2)}(2)] and stoichiometric Cu(OAc)(2). Each transformation uses C—H functionalization methods to form C—C bonds sequentially, with the indeno furanone synthesis featuring a C—O bond formation as the terminating step. This work demonstrates the power of ruthenium-catalyzed alkenylation as a platform reaction to develop more complex transformations, with multiple C—H functionalization steps taking place in a single operation to access novel carbocyclic structures. WILEY-VCH Verlag 2014-02-03 2014-01-22 /pmc/articles/PMC4265981/ /pubmed/24453063 http://dx.doi.org/10.1002/anie.201309114 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Mehta, Vaibhav P García-López, José-Antonio Greaney, Michael F Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title | Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title_full | Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title_fullStr | Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title_full_unstemmed | Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title_short | Ruthenium-Catalyzed Cascade C—H Functionalization of Phenylacetophenones** |
title_sort | ruthenium-catalyzed cascade c—h functionalization of phenylacetophenones** |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4265981/ https://www.ncbi.nlm.nih.gov/pubmed/24453063 http://dx.doi.org/10.1002/anie.201309114 |
work_keys_str_mv | AT mehtavaibhavp rutheniumcatalyzedcascadechfunctionalizationofphenylacetophenones AT garcialopezjoseantonio rutheniumcatalyzedcascadechfunctionalizationofphenylacetophenones AT greaneymichaelf rutheniumcatalyzedcascadechfunctionalizationofphenylacetophenones |