The Journal of Organic Chemistry

Direct synthesis of cyclic ketals of acetophenones by palladium-catalyzed arylation of hydroxyalkyl vinyl ethers

M Larhed, A Hallberg

Index: Larhed, Mats; Hallberg, Anders Journal of Organic Chemistry, 1997 , vol. 62, # 22 p. 7858 - 7862

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Citation Number: 54

Abstract

Reaction of 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, or di (ethylene glycol) vinyl ether with aryl triflates, aryl bromides, or iodobenzene in presence of a catalytical amount of palladium acetate and the bidentate ligand DPPP provides a direct entry to cyclic ketals of acetophenones. It is postulated that the reaction proceeds via an initial α-arylation of the vinyl ethers to give labile aryl vinyl ether intermediates, which undergo subsequent ...