Substrate or Solvent-Controlled Pd-II-Catalyzed Regioselective Arylation of Quinolin-4(1H)-ones Using Diaryliodonium Salts: Facile Access to Benzoxocine and Aaptamine Analogues
- Authors
- Mehra, Manish K.; Sharma, Shivani; Rangan, Krishnan; Kumar, Dalip
- Issue Date
- May-2020
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- C-H functionalization; Quinolin-4(1H)-one; Diaryliodonium salts; Palladium catalyst; Regioselectivety
- Citation
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2020, no.16, pp.2409 - 2413
- Journal Title
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 2020
- Number
- 16
- Start Page
- 2409
- End Page
- 2413
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/84765
- DOI
- 10.1002/ejoc.202000013
- ISSN
- 1434-193X
- Abstract
- Regioselective C3, C5, and C8 arylation of quinolin-4(1H)-ones have been accomplished either by substrate-control or by tuning the reaction solvent. A variety of aryl(mesityl)iodonium triflates could smoothly deliver arylated products in good to excellent yields. Additionally, it offers great flexibility by arylating medicinally potent quinolone related heterocycles such as acridin-9(10H)-one, and phenanthridin-6(5H)-one under standard reaction conditions. This strategy was further extended with diphenyleneiodonium triflate to access oxacine fused quinolines. The post-modifications of synthesized products enhance the further utility of this protocol in organic synthesis. To the best of our knowledge, this is the first report on C5 arylation of quinolin-4(1H)-ones using iodine(III) reagents.
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