期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 359, 期 18, 页码 3261-3269出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700626
关键词
C-H activation; benzodiazepine; photocatalysis; palladacycle; DFT
资金
- EPSRC [EP/M507568/1]
- AstraZeneca [EP/M507568/1]
- Tocris [EP/M507568/1]
- Royal Thai Government
- Engineering and Physical Sciences Research Council [1509523] Funding Source: researchfish
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.
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