Tandem Nickel-Catalyzed Dimerization/(4+2) Cycloaddition of Terminal Alkynes with Four-Membered Ring Ketones

Barday, Manuel, Nicolas, Eva, Higginson, Bradley, Delmotte, Francois, Appelmans, Martin and Aissa, Christophe ORCID: 0000-0003-0750-9435 (2022) Tandem Nickel-Catalyzed Dimerization/(4+2) Cycloaddition of Terminal Alkynes with Four-Membered Ring Ketones. SYNTHESIS-STUTTGART, 54 (04). pp. 1081-1090.

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Official URL: http://dx.doi.org/10.1055/a-1671-8497

Abstract

<jats:title>Abstract</jats:title><jats:p>Controlling the behavior of terminal alkynes in metal-catalyzed intermolecular tandem reactions is a formidable challenge despite the potential advantage offered by these strategies in modern synthesis. Herein, we describe that a nickel catalyst enables a tandem process involving the rapid dimerization of terminal alkynes into 1,3-enynes and the cycloaddition of these intermediates with an azetidinone, an oxetanone or benzocyclobutenones. Significantly, the slow or sequential addition of reagents and catalysts is not required to orchestrate their reactivity. These results are in stark contrast with previous cycloadditions of terminal alkynes with strained four-membered ring substrates, which previously led to oligomerization or cyclotrimerization, except in the case of tert-butylacetylene.</jats:p>

Item Type:	Article
Uncontrolled Keywords:	carbon-carbon bond activation, nickel, catalysis, azetidinone, oxetanone, benzocyclobutenones, tandem
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	23 Nov 2021 08:12
Last Modified:	18 Jan 2023 21:24
DOI:	10.1055/a-1671-8497
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3143671