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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

Solvent-free synthesis and key intermediate isolation in Ni2Dy2 catalyst development in the domino ring-opening electrocyclization reaction of furfural and amines
Solvent-free synthesis and key intermediate isolation in Ni2Dy2 catalyst development in the domino ring-opening electrocyclization reaction of furfural and amines
A solvent-free methodology that yields trans-4,5-diaminocyclopent-2-enones, main domains of natural products and 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.
0022-3263
Sampani, Stavroula I.
346af07d-2a76-47b8-b21d-7416ebb69efc
McGown, Andrew
5809e935-f2bc-4222-8757-f8a07296bcb1
Vargas, Alfredo
81648c3f-59d5-4d8d-ad72-273ec8229054
Abdul-Sada, Alaa
03b55c32-8062-4b73-926d-f243ca078a83
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Kostakis, George E.
dd72c724-c82e-4891-aa68-ccdb42cc6cb8
Sampani, Stavroula I.
346af07d-2a76-47b8-b21d-7416ebb69efc
McGown, Andrew
5809e935-f2bc-4222-8757-f8a07296bcb1
Vargas, Alfredo
81648c3f-59d5-4d8d-ad72-273ec8229054
Abdul-Sada, Alaa
03b55c32-8062-4b73-926d-f243ca078a83
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Kostakis, George E.
dd72c724-c82e-4891-aa68-ccdb42cc6cb8

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. Journal of Organic Chemistry. (doi:10.1021/acs.joc.9b00608).

Record type: Article

Abstract

A solvent-free methodology that yields trans-4,5-diaminocyclopent-2-enones, main domains of natural products and 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.

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Accepted/In Press date: 10 May 2019
e-pub ahead of print date: 10 May 2019

Identifiers

Local EPrints ID: 430905
URI: https://eprints.soton.ac.uk/id/eprint/430905
ISSN: 0022-3263
PURE UUID: 8401ac66-4dc2-41e1-bd45-8f52caec2293
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 17 May 2019 16:30
Last modified: 20 Jul 2019 01:10

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Contributors

Author: Stavroula I. Sampani
Author: Andrew McGown
Author: Alfredo Vargas
Author: Alaa Abdul-Sada
Author: Simon J. Coles ORCID iD
Author: John Spencer
Author: George E. Kostakis

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