Cargando…

Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes

[Image: see text] The three-component coupling reaction of 1,1-dibromoalkenes 1, vinylzinc chloride 2, and carbon soft nucleophiles 3 was realized in the presence of the catalytic palladium/Xantphos species, and 1,3-disubstituted allenic products 5 were obtained in yields of up to 77%. The successiv...

Descripción completa

Detalles Bibliográficos
Autores principales: Sawano, Eri, Ogasawara, Masamichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868900/
https://www.ncbi.nlm.nih.gov/pubmed/31763575
http://dx.doi.org/10.1021/acsomega.9b03444
_version_ 1783472370630000640
author Sawano, Eri
Ogasawara, Masamichi
author_facet Sawano, Eri
Ogasawara, Masamichi
author_sort Sawano, Eri
collection PubMed
description [Image: see text] The three-component coupling reaction of 1,1-dibromoalkenes 1, vinylzinc chloride 2, and carbon soft nucleophiles 3 was realized in the presence of the catalytic palladium/Xantphos species, and 1,3-disubstituted allenic products 5 were obtained in yields of up to 77%. The successive two palladium-catalyzed processes, namely the cross-coupling reaction and the allylic substitution, assembled 5 from the easily accessible starting compounds.
format Online
Article
Text
id pubmed-6868900
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-68689002019-11-22 Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes Sawano, Eri Ogasawara, Masamichi ACS Omega [Image: see text] The three-component coupling reaction of 1,1-dibromoalkenes 1, vinylzinc chloride 2, and carbon soft nucleophiles 3 was realized in the presence of the catalytic palladium/Xantphos species, and 1,3-disubstituted allenic products 5 were obtained in yields of up to 77%. The successive two palladium-catalyzed processes, namely the cross-coupling reaction and the allylic substitution, assembled 5 from the easily accessible starting compounds. American Chemical Society 2019-11-08 /pmc/articles/PMC6868900/ /pubmed/31763575 http://dx.doi.org/10.1021/acsomega.9b03444 Text en Copyright © 2019 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 Sawano, Eri
Ogasawara, Masamichi
Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title_full Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title_fullStr Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title_full_unstemmed Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title_short Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
title_sort palladium-catalyzed three-component coupling of 1,1-dibromoalkenes, vinylzinc chloride, and soft nucleophiles: one-pot synthesis of 1,3-disubstituted allenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6868900/
https://www.ncbi.nlm.nih.gov/pubmed/31763575
http://dx.doi.org/10.1021/acsomega.9b03444
work_keys_str_mv AT sawanoeri palladiumcatalyzedthreecomponentcouplingof11dibromoalkenesvinylzincchlorideandsoftnucleophilesonepotsynthesisof13disubstitutedallenes
AT ogasawaramasamichi palladiumcatalyzedthreecomponentcouplingof11dibromoalkenesvinylzincchlorideandsoftnucleophilesonepotsynthesisof13disubstitutedallenes