Khan, Raysa, Boonseng, Sarote, Kemmitt, Paul D., Felix, Robert, Coles, Simon J., Tizzard, Graham J., Williams, Gareth, Simmonds, Olivia, Harvey, Jessica-Lily, Atack, John  ORCID: https://orcid.org/0000-0002-3410-791X, Cox, Hazel and Spencer, John
2017.
Combining Sanford Arylations on Benzodiazepines with the nuisance effect.
Advanced Synthesis & Catalysis
359
(18)
, pp. 3261-3269.
10.1002/adsc.201700626
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Abstract
5-Phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-ones react under palladium- and visible light photoredox catalysis, in refluxing methanol, with aryldiazonium salts to afford the respective 5-(2-arylphenyl) analogues. With 2- or 4-fluorobenzenediazonium derivatives, both fluoroaryl- and methoxyaryl- products were obtained, the latter resulting from a SNAr on the fluorobenzenediazonium salt (“nuisance effect”). A computational DFT analysis of the palladium-catalysed and the palladium/ruthenium-photocalysed mechanism for the functionalization of benzodiazepines indicated that, in the presence of the photocatalyst, the reaction proceeds via a low-energy SET pathway avoiding the high-energy oxidative addition step in the palladium-only catalysed reaction pathway.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Biosciences |
| Publisher: | Wiley |
| ISSN: | 1615-4150 |
| Date of First Compliant Deposit: | 24 October 2017 |
| Date of Acceptance: | 17 May 2017 |
| Last Modified: | 03 May 2023 00:01 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/105863 |
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