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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.

SUBMITTER: Parasram M

PROVIDER: S-EPMC4291758 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Endo-selective Pd-catalyzed silyl methyl Heck reaction.

Parasram Marvin M Iaroshenko Viktor O VO Gevorgyan Vladimir V

Journal of the American Chemical Society 20141217 52

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. ...[more]

PMID: 25494921

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