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- Title
Synthesis of 3-Fluoro-2-hetarylindoles and 3,3-Difluoro-2-hetarylindolines through Lewis Acid-Catalyzed Formation of 3,3-Difluoroindolium Ions.
- Authors
Fong, Jacqueline Zi Mei; Choo, Simon Sze Shiong; Richard, Jean‐Alexandre; Garland, Marc V.; Guo, Liangfeng; Johannes, Charles W.; Nguyen, Tuan Minh
- Abstract
Synthesis of 3-fluoro-2-hetarylindoles through addition of hetarenes to 3,3-difluoroindolium ions generated in situ by Zn(OTf)2-catalyzed oxazolidine ring opening is described. Indoles, pyrroles and alkyl-substituted furans can be used as hetaryl nucleophiles to afford a range of 3-fluoro-2-hetarylindole products 6 in 56-95 % yields. A diverse array of 3,3-difluorinated 2-hetarylindolines 7 can also be synthesized in 43-84 % yields by a tandem sequential process that involves hetarene nucleophilic addition, HF elimination and fluorocyclization reactions. Our study by 1H NMR and UV/Vis spectroscopy reveals that 3,3-difluorinated 2-hetarylindolines possess interesting substituent-dependent acidochromic properties. UV absorption and fluorescence spectra of selected compounds 6 and 7 are also studied.
- Subjects
CHEMICAL synthesis; INDOLINE; LEWIS acids; FLUORINE; INDOLE derivatives; OXAZOLIDINES; PYRROLES; RING formation (Chemistry)
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 5, p995
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201403443