Volume 22, Issue 15
Preparative Organic Chemistry
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ChemInform Abstract: Synthesis of Enol Esters and Enol Lactones via Palladium-Catalyzed Carbonylation of Aryl and Alkenyl Halides.

I. SHIMOYAMA

I. SHIMOYAMA

Dep. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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Y. ZHANG

Y. ZHANG

Dep. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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G. WU

G. WU

Dep. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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E. NEGISHI

E. NEGISHI

Dep. Chem., Purdue Univ., West Lafayette, IN 47907, USA

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First published: April 16, 1991

Abstract

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ChemInform Abstract

Palladium-catalyzed carbonylation of the γ-iodo ketones (I) and ( IV) forms the enol lactones (III) and (V). Carbonylation of the unsaturated iodo ester (VI) produces the tricyclic lactone (VII). Palladium-catalyzed reaction of the ketones (VIII) with iodobenzene ( IX) and carbon monoxide (II) gives the corresponding enol esters (X), whereas the enol lactones (XII) are obtained from (VIIb) and the vinylic iodides (XI) under analogous conditions.

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