Heck Reaction in Diols
and Cascade Formation of Cyclic Ketals

Matthew McConville; John Blacker; Jianliang Xiao

doi:10.1055/s-0029-1217139

FEATUREARTICLE

Heck Reaction in Diols and Cascade Formation of Cyclic Ketals

Matthew McConville^a, John Blacker^b, Jianliang Xiao*^a
^a Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
Fax: +44(151)7943588; e-Mail: j.xiao@liv.ac.uk ;
^b School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK

Abstract

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Abstract

The regioselective Heck arylation of butyl vinyl ether in alcohols is utilized for the formation of a variety of cyclic ketals. When carried out in ethylene glycol, propane-1,2-diol, or propane-1,3-diol, the palladium-catalyzed arylation afforded dioxolanes or dioxanes directly. With diols such as glycerol, 3-chloropropane-1,2-diol, and 2-methylpropane-1,3-diol, isolation of the Heck adducts and the use of an acid catalyst for the ketalization were necessary; an efficient phosphoric acid was identified. The procedure presented provides a new pathway for the synthesis of cyclic ketals, particularly those that are functionalized.

Key words

ketals - diols - olefins - Heck reaction - homogeneous catalysis

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References

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