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Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination

[Image: see text] The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl(2)(p-cymene)](2) as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds u...

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Autores principales: Tan, Eric, Konovalov, Andrey I., Fernández, Gabriela A., Dorel, Ruth, Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5679662/
https://www.ncbi.nlm.nih.gov/pubmed/28976200
http://dx.doi.org/10.1021/acs.orglett.7b02655
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author Tan, Eric
Konovalov, Andrey I.
Fernández, Gabriela A.
Dorel, Ruth
Echavarren, Antonio M.
author_facet Tan, Eric
Konovalov, Andrey I.
Fernández, Gabriela A.
Dorel, Ruth
Echavarren, Antonio M.
author_sort Tan, Eric
collection PubMed
description [Image: see text] The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl(2)(p-cymene)](2) as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds under similar conditions and also shows wide functional group tolerance. Both reactions proceed through metalation, insertion of the alkyne, and bromide elimination.
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spelling pubmed-56796622017-11-13 Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination Tan, Eric Konovalov, Andrey I. Fernández, Gabriela A. Dorel, Ruth Echavarren, Antonio M. Org Lett [Image: see text] The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl(2)(p-cymene)](2) as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds under similar conditions and also shows wide functional group tolerance. Both reactions proceed through metalation, insertion of the alkyne, and bromide elimination. American Chemical Society 2017-10-04 2017-10-20 /pmc/articles/PMC5679662/ /pubmed/28976200 http://dx.doi.org/10.1021/acs.orglett.7b02655 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Tan, Eric
Konovalov, Andrey I.
Fernández, Gabriela A.
Dorel, Ruth
Echavarren, Antonio M.
Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title_full Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title_fullStr Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title_full_unstemmed Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title_short Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination
title_sort ruthenium-catalyzed peri- and ortho-alkynylation with bromoalkynes via insertion and elimination
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5679662/
https://www.ncbi.nlm.nih.gov/pubmed/28976200
http://dx.doi.org/10.1021/acs.orglett.7b02655
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