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Synthesis 2010(2): 349-360  
DOI: 10.1055/s-0029-1217139
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Heck Reaction in Diols and Cascade Formation of Cyclic Ketals

Matthew McConvillea, John Blackerb, 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
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Publikationsverlauf

Received 16 September 2009
Publikationsdatum:
20. November 2009 (online)

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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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