Endo-selective pd-catalyzed silyl methyl heck reaction

Marvin Parasram; Viktor O. Iaroshenko; Vladimir Gevorgyan

doi:10.1021/ja5104525

Endo-selective pd-catalyzed silyl methyl heck reaction

Marvin Parasram, Viktor O. Iaroshenko, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

76 Scopus citations

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 language	English (US)
Pages (from-to)	17926-17929
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	52
DOIs	https://doi.org/10.1021/ja5104525
State	Published - Dec 31 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja5104525

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title = "Endo-selective pd-catalyzed silyl methyl heck reaction",

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.",

author = "Marvin Parasram and Iaroshenko, {Viktor O.} and Vladimir Gevorgyan",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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AU - Parasram, Marvin

AU - Iaroshenko, Viktor O.

AU - Gevorgyan, Vladimir

PY - 2014/12/31

Y1 - 2014/12/31

N2 - 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.

AB - 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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Endo-selective pd-catalyzed silyl methyl heck reaction

Abstract

ASJC Scopus subject areas

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