4.7 Article

Combining Sanford Arylations on Benzodiazepines with the Nuisance Effect

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

  1. EPSRC [EP/M507568/1]
  2. AstraZeneca [EP/M507568/1]
  3. Tocris [EP/M507568/1]
  4. Royal Thai Government
  5. Engineering and Physical Sciences Research Council [1509523] Funding Source: researchfish

向作者/读者索取更多资源

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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