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Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by nickel-catalyzed

Abstract

A highly efficient and simple route for the synthesis of multi-substituted allenes has been developed by Nickel catalyzed the SN2’ substitution reaction of propargyl esters with organic aluminium reagents under mild conditions, giving the corresponding product multi-substituted allenes in good to excellent yields (up to 94%) and high selectivities (up to 99%) at 60 oC for 6h in THF. The 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, 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. This process was simple and easily performed, which provides an efficient method for the synthesis of multi-substituted allenes derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

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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, Accepted Manuscript
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    Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by nickel-catalyzed

    X. shao, Z. Zhang, Q. Li and Z. Zhao, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB00781K

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