Endo-selective pd-catalyzed silyl methyl heck reaction

Marvin Parasram, Viktor O. Iaroshenko, Vladimir Gevorgyan

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)17926-17929
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number52
DOIs
StatePublished - Dec 31 2014
Externally publishedYes

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Palladium
Ethers
Phenols
Silicon
Atoms

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Endo-selective pd-catalyzed silyl methyl heck reaction. / Parasram, Marvin; Iaroshenko, Viktor O.; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 136, No. 52, 31.12.2014, p. 17926-17929.

Research output: Contribution to journalArticle

Parasram, Marvin ; Iaroshenko, Viktor O. ; Gevorgyan, Vladimir. / Endo-selective pd-catalyzed silyl methyl heck reaction. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 52. pp. 17926-17929.
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