[reaction: see text] A palladium-catalyzed coupling reaction of phenyliodonium zwitterions with aryl boronic acids has been developed. The unique characteristics of the mild reaction conditions and convenient synthetic accessibility of phenyliodonium zwitterions make this method a valuable tool for generating diversified 3-aryl-4-hydroxycoumarins.

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http://dx.doi.org/10.1021/ol020159bDOI Listing

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The reaction of β-dicarbonyl phenyliodonium ylides with diphenylketene at room temperature affords mixtures of lactone and aurone derivatives. The initial electrophilic attack of the iodonium ylide on the C(β) position of the diphenylketene, followed by cyclization of the zwitterionic species, and subsequent ejection of iodobenzene, affords the lactone and aurone cycloadducts. Treatment of β-dicarbonyl iodonium ylides with acyl chlorides yields α-chloroenones with good to excellent yields.

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[reaction: see text] A palladium-catalyzed coupling reaction of phenyliodonium zwitterions with aryl boronic acids has been developed. The unique characteristics of the mild reaction conditions and convenient synthetic accessibility of phenyliodonium zwitterions make this method a valuable tool for generating diversified 3-aryl-4-hydroxycoumarins.

View Article and Find Full Text PDF

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