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Tandem Pd(II)-Catalyzed Vinyl Ether Exchange-Claisen Rearrangement as a Facile Approach to γ,δ-Unsaturated Aldehydes

Xudong Wei,* Jon C. Lorenz, Suresh Kapadia, Anjan Saha, Nizar Haddad, Carl A. Busacca, and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877, Email:

X. Wei, J. C. Lorenz, S. Kapadia, A. Saha, N. Haddad, C. A. Busacca, C. H. Senanayake, J. Org. Chem., 2007, 72, 4250-4253.

DOI: 10.1021/jo062548f (free Supporting Information)

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A sequential allyl vinyl ether formation-Claisen rearrangement process catalyzed by a palladium(II)-phenanthroline complex provides a convenient approach to γ,δ-unsaturated aldehydes under mild conditions that avoid the use of toxic Hg(II) catalysts. The new methodology has been successfully demonstrated on kilogram scale.

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Key Words

Claisen Rearrangement, Aldehydes, Allylation

ID: J42-Y2007-1670