Bis(triarylmethylium)-mediated diaryl ether synthesis: Oxidative arylation of phenols with N,N-dialkyl-4-phenylthioanilines

Journal of the American Chemical Society

Volumn 127, Issue 27, 2005, Pages 9696-9697

  Saitoh, Terunobu ^a   Ichikawa, Junji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 PHENYLTHIOANILINE DERIVATIVE; ANILINE DERIVATIVE; ETHER DERIVATIVE; FUNCTIONAL GROUP; METHYL GROUP; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 22144431535     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051839n     Document Type: Article

References (31)

1. For a review, see: Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135.
2. For reviews on diaryl ether synthesis, see: (a) Sawyer, J. S. Tetrahedron 2000, 56, 5045.
3. (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
4. (c) Lindley, J. Tetrahedron 1984, 40, 1433.
5. Luo, Y.; Wu, J. X.; Ren, R. X. Synlett 2003, 1734.
6. Gujadhur, R. K.; Bates, C. G.; Verkataraman, D. Org. Lett. 2001, 3, 4315.
7. Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
8. Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
9. (a) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224 and references therein.
10. (b) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
11. Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169.
12. (a) Wang, H.; Gabbaï, F. P. Org. Lett. 2005, 7, 283.
13. (b) Wang, H.; Webster, C. E.; Pérez, L. M.; Hall, M. B.; Gabbaï. F. P. J. Am. Chem. Soc. 2004, 126, 8189.
14. Saitoh, T.; Yoshida, S.; Ichikawa, J. Org. Lett. 2004, 6, 4563.
15. (a) Higuchi, H.; Ohta, E.; Kawai, H.; Fujiwara, K.; Tsuji, T.; Suzuki, T. J. Org. Chem. 2003, 68, 6605 and references therein.
16. (b) Carey, K. A.; Clegg, W.; Elsegood, M. R. J.; Golding, B. T.; Hill, M. N. S.; Haskill, H. J. Chem. Soc., Perkin Trans. 1 2002, 2673.
17. For a review, see: Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
18. 10
19. For the oxidative phenolic coupling promoted by thallium(III) trinitrate, see: (a) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1990, 28, 4053 and references therein.
20. See also: (b) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684.
21. The less electron-rich 4-methoxyphenyl phenyl sulfide did not act as an aryl donor.
22. Becker, H.-D. The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; Wiley: Chichester, 1974; Part 2, Chapter 7.
23. Kluge, R. J. Prakt. Chem. 1996, 338, 287.
24. Ho, T.-L. Synthesis 1973, 347.
25. Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Angew. Chem., Int. Ed. 2002, 41, 4532 and references therein.
26. Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.: Pergamon Press: New York, 1991.
27. (a) Rhile, I. J.; Mayer, J. M. J. Am. Chem. Soc. 2004, 126, 12718.
28. (b) Lucarini, M.; Muanaini, V.; Pedulli, G. F.; Guerra, M. J. Am. Chem. Soc. 2003, 125, 8318.
29. 2 at 5 K suggested the existence of a radical species.
30. 24 ethylation of 7 was effected on the sulfur atom to yield the corresponding sulfonium salt in 13% yield.
31. Ichinose, Y.; Nozaki, K.; Wakamatsu, K.; Oshima, K. Tetrahedron Lett. 1987, 28, 3709.