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Issue 26, 2018
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Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst

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Abstract

A highly efficient and simple route for the synthesis of multi-substituted allenes has been developed by a nickel catalyzed SN2′ substitution reaction of propargyl esters with organic aluminium reagents under mild conditions, which gave the corresponding multi-substituted allenes in good to excellent yields (up to 92%) and high selectivities (up to 99%) at 60 °C for 6 h in THF. Aryls bearing electron-donating or electron-withdrawing groups in propargyl esters gave products in good yields. In addition, the multi-substituted allenes bearing a thienyl or a pyridyl group were obtained in 95–97% selectivities with isolated yields of 72–83%. Furthermore, the SN2′ substitution reaction worked efficiently with propargyl carbonate compounds as well. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Graphical abstract: Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst

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Publication details

The article was received on 03 Apr 2018, accepted on 11 Jun 2018 and first published on 11 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB00781K
Citation: Org. Biomol. Chem., 2018,16, 4797-4806
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    Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst

    X. B. Shao, Z. Zhang, Q. H. Li and Z. G. Zhao, Org. Biomol. Chem., 2018, 16, 4797
    DOI: 10.1039/C8OB00781K

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