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Palladium-catalysed atom-economical synthesis of conjugated dienals from terminal acetylenes and acrolein

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Abstract

Conjugated (E,E)-dienals are versatile synthetic intermediates owing to their trifunctional, electrophilic nature and the prevalence of the (E,E)-diene in a wide range of functional molecules. It is shown herein that (E,E)-dienals can be readily prepared in two palladium-catalysed steps from simple, unactivated starting materials; terminal acetylenes and acrolein can be coupled via conjugate addition, followed by alkyne isomerisation. This procedure provides a highly atom-economical, redox-neutral and practical method to prepare a range of conjugated (E,E)-dienals in good yields and diastereoselectivities.

Graphical abstract: Palladium-catalysed atom-economical synthesis of conjugated dienals from terminal acetylenes and acrolein

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Publication details

The article was received on 13 Apr 2017, accepted on 11 May 2017 and first published on 12 May 2017


Article type: Communication
DOI: 10.1039/C7CC02767B
Citation: Chem. Commun., 2017, Advance Article
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    Palladium-catalysed atom-economical synthesis of conjugated dienals from terminal acetylenes and acrolein

    Z. Hearne and C. Li, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02767B

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