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Copper-Catalyzed Reductive Ireland-Claisen Rearrangements of Propargylic Acrylates and Allylic Allenoates

Siyuan Guo, Kong Ching Wong, Stephan Scheeff, Zhuo He, Wesley Ting Kwok Chan, Kam-Hung Low and Pauline Chiu*

*Department of Chemistry and The State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China, Email:

S. Guo, K. C. Wong, S. Scheeff, Z. He, W. T. K. Chan, K.-H. Low, P. Chiu, J. Org. Chem., 2022, 87, 429-452.

DOI: 10.1021/acs.joc.1c02455

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The copper-catalyzed reductive Ireland-Claisen rearrangement of propargylic acrylates led to 3,4-allenoic acids in the presence of silanes or pinacolborane as stoichiometric reducing agents and triethylphosphite as a ligand. A copper-catalyzed reductive Ireland-Claisen rearrangement of allylic 2,3-allenoates using pinacolborane provides various 1,5-dienes in excellent yields.

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Key Words

Ireland-Claisen Rearrangement, Allenes. Pinacolborane

ID: J42-Y2022