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Combining Sanford Arylations on Benzodiazepines with the nuisance effect

Khan, Raysa, Boonseng, Sarote, Kemmitt, Paul D., Felix, Robert, Coles, Simon J., Tizzard, Graham J., Williams, Gareth, Simmonds, Olivia, Harvey, Jessica-Lily, Atack, John, 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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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: Biosciences
Publisher: Wiley
ISSN: 1615-4150
Date of First Compliant Deposit: 24 October 2017
Date of Acceptance: 17 May 2017
Last Modified: 25 Oct 2017 12:22

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