Polyfluorination of aryl alkyl sulfides by IF5 with concomitant migration of the arylthio group

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2873-2874

  Ayuba, Shinichi ^a   Fukuhara, Tsuyoshi ^a   Hara, Shoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; FLUORINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE;

ARTICLE; CHEMICAL REACTION; FLUORINATION;

EID: 0141631705     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034912s     Document Type: Article

References (7)

1. Hiyama, T. In Organofluorine Compounds; Springer: Berlin, 2000; p 59 and refernces are cited therein.
2. Ayuba, S.; Yoneda, N.; Fukuhara, T.; Hara, S. Bull. Chem. Soc. Jpn. 2002, 75, 1597.
3. Recently, Motherwell et al. reported an introduction of fluorine atoms at the α- and β-positions of the sulfur group of arylthiolactames using iodotoluene difluoride without migration of the arylthio group; see: Greaney, M. F.; Motherwell, W. B.; Tocher, D. A. Tetrahedron Lett. 2001, 42, 8523.
4. 5
5. Rozen, S.; Brand, M. J. Org. Chem. 1985, 50, 3342.
6. As for the addition of IF to double bonds, see: Yagupolskii, L. M. In Organo-Fluorine Compounds; Baasner, B., Hagemann, H., Tatlow, J. C., Eds.; Georg Thime; Stuttgart, 2000, p 234 and references cited therein.
7. A similar mechanism involving episulfonium ion was postulated in an electrochemical fluorination of vinyl sulfids; see: Andres, D. F.; Laurent, E. G.; Marquet, B. S. Tetrahedron 1995, 51, 2605.