Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**

1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C–H activation, involving a hi...

Descripción completa

Detalles Bibliográficos
Autores principales: Burns, David J, Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464529/
https://www.ncbi.nlm.nih.gov/pubmed/25048465
http://dx.doi.org/10.1002/anie.201406072
_version_ 1782375992019386368
author Burns, David J
Lam, Hon Wai
author_facet Burns, David J
Lam, Hon Wai
author_sort Burns, David J
collection PubMed
description 1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C–H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.
format Online
Article
Text
id pubmed-4464529
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher WILEY-VCH Verlag
record_format MEDLINE/PubMed
spelling pubmed-44645292015-06-17 Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations** Burns, David J Lam, Hon Wai Angew Chem Int Ed Engl Communications 1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C–H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products. WILEY-VCH Verlag 2014-09-08 2014-07-22 /pmc/articles/PMC4464529/ /pubmed/25048465 http://dx.doi.org/10.1002/anie.201406072 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/3.0/ 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
Burns, David J
Lam, Hon Wai
Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title_full Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title_fullStr Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title_full_unstemmed Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title_short Catalytic 1,4-Rhodium(III) Migration Enables 1,3-Enynes to Function as One-Carbon Oxidative Annulation Partners in C–H Functionalizations**
title_sort catalytic 1,4-rhodium(iii) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in c–h functionalizations**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464529/
https://www.ncbi.nlm.nih.gov/pubmed/25048465
http://dx.doi.org/10.1002/anie.201406072
work_keys_str_mv AT burnsdavidj catalytic14rhodiumiiimigrationenables13enynestofunctionasonecarbonoxidativeannulationpartnersinchfunctionalizations
AT lamhonwai catalytic14rhodiumiiimigrationenables13enynestofunctionasonecarbonoxidativeannulationpartnersinchfunctionalizations

Ejemplares similares