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J Org Chem. 2007 Aug 17;72(17):6390-6. Epub 2007 Jul 21.

Highly regioselective internal heck arylation of hydroxyalkyl vinyl ethers by aryl halides in water.

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  • 1Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden.

Abstract

Highly regioselective and fast Pd(0)-catalyzed internal alpha-arylation of ethylene glycol vinyl ether with aryl halides was shown to be possible in water without the need for any halide scavengers or ionic liquid additives. This presents, to our knowledge, the first case of water being utilized in the selective arylation of electron-rich olefins. Resulting alpha-products were hydrolyzed and isolated as corresponding acetophenones in good to excellent yields when using aryl bromides and with good to moderate yields in the case of aryl iodides. Microwave irradiation was shown to be beneficial in activation of aryl chlorides toward the internal Heck arylation. The scope of the protocol was further increased to include different hydroxyalkyl vinyl ethers, these all giving selectively only branched alpha-products. Finally, the active role of the hydroxy group in directing the regioselectivity toward internal arylation of electron-rich olefins, even in nonpolar toluene, was revealed.

PMID:
17658848
DOI:
10.1021/jo0705768
[PubMed - indexed for MEDLINE]
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