Tandem Pd(II)-Catalyzed Vinyl Ether Exchange−Claisen Rearrangement as a Facile Approach to γ,δ-Unsaturated Aldehydes
The Journal of Organic Chemistry2007Vol. 72(11), pp. 4250–4253
Citations Over TimeTop 19% of 2007 papers
Xudong Wei, Jon C. Lorenz, Suresh Kapadia, Anjan K. Saha, Nizar Haddad, Carl A. Busacca, Chris H. Senanayake
Abstract
A sequential allyl vinyl ether formation-Claisen rearrangement process catalyzed by a palladium(II)-phenanthroline complex is reported. The effects of allylic alcohol structure, type of vinylating agent, and palladium catalysts are discussed. This method provides a convenient approach to gamma,delta-unsaturated aldehydes under mild conditions that avoid the use of toxic Hg(II) catalysts. The new methodology has been successfully demonstrated on the kilogram scale.
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