Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands

Palladium-catalyzed 1,4-difunctionalizations of isoprene that produce skipped polyenes are reported. Complex isomeric product mixtures are possible as a result of the difficult-to-control migratory insertion of isoprene into a Pd–alkenyl bond, but good site selectivity has been achieved using easily...

Descripción completa

Detalles Bibliográficos
Autores principales: McCammant, Matthew S., Sigman, Matthew S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334162/
https://www.ncbi.nlm.nih.gov/pubmed/25705367
http://dx.doi.org/10.1039/c4sc03074e
_version_ 1782358146827681792
author McCammant, Matthew S.
Sigman, Matthew S.
author_facet McCammant, Matthew S.
Sigman, Matthew S.
author_sort McCammant, Matthew S.
collection PubMed
description Palladium-catalyzed 1,4-difunctionalizations of isoprene that produce skipped polyenes are reported. Complex isomeric product mixtures are possible as a result of the difficult-to-control migratory insertion of isoprene into a Pd–alkenyl bond, but good site selectivity has been achieved using easily accessible pyrox ligands. Mechanistic studies suggest that the control of insertion is the result of the unique electronic asymmetry and steric properties of the ligand.
format Online
Article
Text
id pubmed-4334162
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-43341622016-01-31 Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands McCammant, Matthew S. Sigman, Matthew S. Chem Sci Chemistry Palladium-catalyzed 1,4-difunctionalizations of isoprene that produce skipped polyenes are reported. Complex isomeric product mixtures are possible as a result of the difficult-to-control migratory insertion of isoprene into a Pd–alkenyl bond, but good site selectivity has been achieved using easily accessible pyrox ligands. Mechanistic studies suggest that the control of insertion is the result of the unique electronic asymmetry and steric properties of the ligand. Royal Society of Chemistry 2015-02-01 2014-11-28 /pmc/articles/PMC4334162/ /pubmed/25705367 http://dx.doi.org/10.1039/c4sc03074e Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
McCammant, Matthew S.
Sigman, Matthew S.
Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title_full Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title_fullStr Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title_full_unstemmed Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title_short Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
title_sort development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4334162/
https://www.ncbi.nlm.nih.gov/pubmed/25705367
http://dx.doi.org/10.1039/c4sc03074e
work_keys_str_mv AT mccammantmatthews developmentandinvestigationofasiteselectivepalladiumcatalyzed14difunctionalizationofisopreneusingpyridineoxazolineligands
AT sigmanmatthews developmentandinvestigationofasiteselectivepalladiumcatalyzed14difunctionalizationofisopreneusingpyridineoxazolineligands

Ejemplares similares