Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes

[Image: see text] An efficient method for the construction of Csp(2)–Csp(3) bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermed...

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Autores principales: Saini, Vaneet, O’Dair, Mark, Sigman, Matthew S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4308737/
https://www.ncbi.nlm.nih.gov/pubmed/25555197
http://dx.doi.org/10.1021/ja511640g
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author Saini, Vaneet
O’Dair, Mark
Sigman, Matthew S.
author_facet Saini, Vaneet
O’Dair, Mark
Sigman, Matthew S.
author_sort Saini, Vaneet
collection PubMed
description [Image: see text] An efficient method for the construction of Csp(2)–Csp(3) bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks.
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spelling pubmed-43087372016-01-02 Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes Saini, Vaneet O’Dair, Mark Sigman, Matthew S. J Am Chem Soc [Image: see text] An efficient method for the construction of Csp(2)–Csp(3) bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks. American Chemical Society 2015-01-02 2015-01-21 /pmc/articles/PMC4308737/ /pubmed/25555197 http://dx.doi.org/10.1021/ja511640g Text en Copyright © 2015 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 Saini, Vaneet
O’Dair, Mark
Sigman, Matthew S.
Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title_full Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title_fullStr Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title_full_unstemmed Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title_short Synthesis of Highly Functionalized Tri- and Tetrasubstituted Alkenes via Pd-Catalyzed 1,2-Hydrovinylation of Terminal 1,3-Dienes
title_sort synthesis of highly functionalized tri- and tetrasubstituted alkenes via pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4308737/
https://www.ncbi.nlm.nih.gov/pubmed/25555197
http://dx.doi.org/10.1021/ja511640g
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