Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction

[Image: see text] A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for...

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Autores principales: Parasram, Marvin, Iaroshenko, Viktor O., Gevorgyan, Vladimir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4291758/
https://www.ncbi.nlm.nih.gov/pubmed/25494921
http://dx.doi.org/10.1021/ja5104525
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author Parasram, Marvin
Iaroshenko, Viktor O.
Gevorgyan, Vladimir
author_facet Parasram, Marvin
Iaroshenko, Viktor O.
Gevorgyan, Vladimir
author_sort Parasram, Marvin
collection PubMed
description [Image: see text] A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.
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spelling pubmed-42917582015-12-11 Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction Parasram, Marvin Iaroshenko, Viktor O. Gevorgyan, Vladimir J Am Chem Soc [Image: see text] A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols. American Chemical Society 2014-12-11 2014-12-31 /pmc/articles/PMC4291758/ /pubmed/25494921 http://dx.doi.org/10.1021/ja5104525 Text en Copyright © 2014 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 Parasram, Marvin
Iaroshenko, Viktor O.
Gevorgyan, Vladimir
Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title_full Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title_fullStr Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title_full_unstemmed Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title_short Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
title_sort endo-selective pd-catalyzed silyl methyl heck reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4291758/
https://www.ncbi.nlm.nih.gov/pubmed/25494921
http://dx.doi.org/10.1021/ja5104525
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AT iaroshenkoviktoro endoselectivepdcatalyzedsilylmethylheckreaction
AT gevorgyanvladimir endoselectivepdcatalyzedsilylmethylheckreaction

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