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Development of an anomalous Heck reaction: skeletal rearrangement of divinyl and enyne carbinols.

ABSTRACT: [reaction: see text] A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri- or tetrasubstituted olefins in good yields (up to 83%) is described. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress beta-hydride elimination of organopalladium intermediates appears to be critical to the success of these processes.

SUBMITTER: Ndungu JM

PROVIDER: S-EPMC3342700 | biostudies-literature | 2005 Dec

REPOSITORIES: biostudies-literature

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Development of an anomalous Heck reaction: skeletal rearrangement of divinyl and enyne carbinols.

Ndungu J Maina JM Larson Kimberly K KK Sarpong Richmond R

Organic letters 20051201 26

[reaction: see text] A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri- or tetrasubstituted olefins in good yields (up to 83%) is described. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress beta-hydride elimination of organopalladium intermediates appears to be critical to the success of these processes. ...[more]

PMID: 16354081

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