4.6 Article

Achieving Vinylic Selectivity in Mizoroki-Heck Reaction of Cyclic Olefins

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 19, Pages 6014-6020

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201204427

Keywords

arylation; Heck reaction; isomerization; olefins; vinylic selectivity

Funding

  1. Singapore National Research Foundation [NRF-RF2008-10]
  2. Nanyang Technological University

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In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions.

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