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Issue 11, 2017
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Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

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Abstract

1,6-Dichlorohexa-2,4-diyne undergoes nickel-catalyzed double substitution with aryl and alkenyl Grignard reagents to provide substituted ene-yne-enes. The reaction is formally an extension of the well-described SN2′-allylic and -propargylic substitution reactions but the mechanism is considerably more complex. The products might function as building blocks for conjugated polymers.

Graphical abstract: Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

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Publication details

The article was received on 06 Mar 2017, accepted on 26 Apr 2017 and first published on 26 Apr 2017


Article type: Paper
DOI: 10.1039/C7CY00429J
Citation: Catal. Sci. Technol., 2017,7, 2347-2355
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    Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne

    G. Wang, E. Lindeboom, C. van Heerewaarden and A. J. Minnaard, Catal. Sci. Technol., 2017, 7, 2347
    DOI: 10.1039/C7CY00429J

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