Solvent-free synthesis and key intermediate isolation in Ni2Dy2 catalyst development in the domino ring-opening electrocyclization reaction of furfural and amines

Sampani, Stavroula I, McGown, Andrew, Vargas, Alfredo, Abdul-Sada, Alaa, Tizzard, Graham J, Coles, Simon J, Spencer, John and Kostakis, George E (2019) Solvent-free synthesis and key intermediate isolation in Ni2Dy2 catalyst development in the domino ring-opening electrocyclization reaction of furfural and amines. The Journal of Organic Chemistry. ISSN 0022-3263

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Abstract

A solvent-free methodology that yields trans-4,5-diaminocyclopent-2-enones, main domains of natural products and a variety of N-heterocycles, is described. The bimetallic catalyst [NiII2DyIII2L4(DMF)6] 2(OTf) 2(DMF) (1) promotes the domino reaction of furfural and amines, with loadings as low as 0.01%, under stirring or microwave-assisted conditions to afford the corresponding frameworks in very good to excellent yields. Crystallographic and theoretical studies shed light on the exclusive formation of the trans-diastereoisomers via a 4π-conrotatory electrocyclization process elucidating the key step in the catalytic process.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0146 Inorganic chemistry
Depositing User: Georgios Kostakis
Date Deposited: 10 May 2019 08:24
Last Modified: 01 Jul 2019 13:16
URI: http://sro.sussex.ac.uk/id/eprint/83662

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Project NameSussex Project NumberFunderFunder Ref
Defect dicubane 3d/Dy(III) Coordination Clusters: Heading for materials displaying catalytic propertiesG1632EPSRC-ENGINEERING & PHYSICAL SCIENCES RESEARCH COUNCILEP/M023834/1