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Synfacts 2007(6): 0584-0584  
DOI: 10.1055/s-2007-968574
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Reductive Double Cyclization of Yne-enynals to Furans

Contributor(s): Victor Snieckus, Heiko Scharl
C. H. Oh*, H. M. Park, D. I. Park
Hanyang University, Seoul, Korea
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

A palladium-catalyzed reductive double cyclization of conjugated enynals bearing an alkyne tether leading to 2-(2-methylenecyclo­alkyl)-furans in moderate to excellent yields is reported. Hydropalladation of the internal triple bond with an in situ generated PdOCOH species is proposed as a mechanistic rationale. This is followed by carbonyl oxygen attack of the palladium nucleus and release of CO2 during a hydride transfer reaction.