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Solvent-free synthesis and key intermediate isolation in Ni2Dy2 catalyst development in the domino ring-opening electrocyclization reaction of furfural and amines
journal contribution
posted on 2023-06-09, 17:45 authored by Stavroula Sampani, Andrew McGownAndrew McGown, Alfredo VargasAlfredo Vargas, Alaa Abdul-Sada, Graham J Tizzard, Simon J Coles, John SpencerJohn Spencer, George KostakisGeorge KostakisA 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 4p-conrotatory electrocyclization process elucidating the key step in the catalytic process.
Funding
Defect dicubane 3d/Dy(III) Coordination Clusters: Heading for materials displaying catalytic properties; G1632; EPSRC-ENGINEERING & PHYSICAL SCIENCES RESEARCH COUNCIL; EP/M023834/1
History
Publication status
- Published
File Version
- Accepted version
Journal
The Journal of Organic ChemistryISSN
0022-3263Publisher
American Chemical SocietyExternal DOI
Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2019-05-10First Open Access (FOA) Date
2020-05-10First Compliant Deposit (FCD) Date
2019-05-09Usage metrics
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