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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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Article information


Submitted
06 Mar 2017
Accepted
26 Apr 2017
First published
26 Apr 2017

Catal. Sci. Technol., 2017,7, 2347-2355
Article type
Paper

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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