Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles
Issued Date
2023-05-05
Resource Type
ISSN
00223263
eISSN
15206904
Scopus ID
2-s2.0-85152145402
Journal Title
Journal of Organic Chemistry
Volume
88
Issue
9
Start Page
5403
End Page
5419
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry Vol.88 No.9 (2023) , 5403-5419
Suggested Citation
Uppalabat T., Hassa N., Sawektreeratana N., Leowanawat P., Janthakit P., Nalaoh P., Promarak V., Soorukram D., Reutrakul V., Kuhakarn C. Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles. Journal of Organic Chemistry Vol.88 No.9 (2023) , 5403-5419. 5419. doi:10.1021/acs.joc.2c03045 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/82903
Title
Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles
Author's Affiliation
Other Contributor(s)
Abstract
Persulfate-promoted radical cascade trifluoromethylthiolation and cyclization of 3-alkyl-1-(2-(alkynyl)phenyl)indoles with AgSCF3 were investigated. This protocol provides a novel route to CF3S-substituted indolo[1,2-a]quinoline-7-carbaldehydes and CF3S-substituted indolo[1,2-a]quinoline-7-methanone derivatives via the formation of the C-SCF3 bond and C-C bond and benzylic carbon oxidation in a single step. This reaction can accommodate a broad range of functional groups. The single-crystal X-ray diffraction data confirm the chemical structure of the product. A scale-up experiment and radical inhibition experiments were operated in the reaction system. Photophysical properties of some selected 5-((trifluoromethyl)thio)indolo[1,2-a]quinoline-7-carbaldehydes were studied by UV-visible and fluorescence spectroscopy.