Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling

Mary K. Smith and Jon A. Tunge*

*Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States, Email: tungeku.edu

M. K. Smith, J. A Tunge, Org. Lett., 2017, 19, 5497-5500.

DOI: 10.1021/acs.orglett.7b01751

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Abstract

Conjugated allenynes can be accessed via a decarboxylative coupling of propargyl esters of propiolates. In this process, allenyl-palladium intermediates are coupled with acetylides that are generated in situ to form the conjugated allenynes. Finally, the coupling is demonstrated to occur stereospecifically in an anti-S_N2' fashion to provide a route to enantioenriched allenes.

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stereospecific decarboxylative coupling

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Key Words

allenes, enynes

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ID: J54-Y2017