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Paper | Special issue | Vol 70, No. 1, 2006, pp.309-319
Published online, 7th November, 2006
DOI: 10.3987/COM-06-S(W)24
Synthesis of 2,3-Dihydrobenzo[1,4]dioxins and -oxazins via a Domino Wacker-Heck Reaction

Lutz G. Tietze,* Kristina F. Wilckens, Sinem Yilmaz, Florian Stecker, and Julia Zinngrebe

*Institute of Organic and Biomolecular Chemistry, Georg-August-University, Tammannstr. 2, D-37077 Göttingen, Germany

Abstract

An efficient and operationally simple domino Wacker-Heck reaction of allylic phenols and α,β-unsaturated ketones as well as esters in the presence of catalytic amounts of Pd(TFA)2 and an oxidant for the synthesis of 2,3-dihydrobenzo[1,4]dioxins and 2,3-dihydrobenzo[1,4]oxazins is described. The necessary substrates are prepared by monoallylation of catechol derivatives and ortho-aminophenol.