Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III)

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13596-13597

  Shi, Zhangjie ^a   He, Chuan ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ESTER DERIVATIVE; GOLD; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILVER; SULFONIC ACID DERIVATIVE;

ADDITION REACTION; ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CONCENTRATION RESPONSE; CYCLIZATION; ENERGY YIELD; FRIEDEL CRAFTS REACTION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 6444240772     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046890q     Document Type: Article

References (36)

1. (a) Hashmi, A. S. K. Gold Bull. 2003, 36, 3-9.
2. (b) Hashmi, A. S. K.; Schwarz, L.; Choi, J. H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
3. (c) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1418.
4. (d) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563-4565.
5. (e) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650-12651.
6. (f) Fuchita, Y.; Utsunomiva, Y.; Yasutake, M. J. Chem. Soc., Dalton Trans. 2001, 2330-2334.
7. (g) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
8. (h) Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485-3496.
9. (i) Arcadi, A.; Bianchi, G.; Marinelli, F. Synthesis 2004, 610-618.
10. (j) Dyker, G.; Muth, E.; Hashmi, A. S. K.; Ding, L. Adv. Synth. Catal. 2003, 345, 1247-1252.
11. (k) Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884-6885.
12. (l) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-06.
13. (a) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669-3671.
14. (b) Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964-5965.
15. (a) Olah, G. A. Friedel-Crafts and Related Reactions; Wiley: New York, 1973.
16. For a recent review, see: (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556.
17. (a) Jia, C. G.; Piao, D. G.; Oyamada, J. Z.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992-1995.
18. (b) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305-308.
19. (c) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390-391.
20. (d) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531.
21. (e) Weissman, H.; Song, X. P.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337-338.
22. (f) Matsumoto, T.; Taube, D. J.; Periana, R. A.; Taube, H.; Yoshida, H. J. Am. Chem. Soc. 2000, 122, 7414-7415.
23. (g) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685-2686.
24. (h) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476-1477.
25. (i) Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507.
26. (j) Hennessy, E.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084-12085.
27. (k) Tsukada, N.; Mitsuboshi, T.; Setoguchi, H.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 12102-12103.
28. (l) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579.
29. Liu, C.; Han, X.; Wang, X.; Widenhoefer, A. W. J. Am. Chem. Soc. 2004, 126, 3700-3701.
30. Also, for recent reviews, see: (n) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181-2192. (o) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
31. Also, for recent reviews, see: (n) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181-2192. (o) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
32. (a) Kharasch, M. S.; Isbell, H. S. J. Am. Chem. Soc. 1931, 53, 3053-3059.
33. (b) de Graaf, P. W. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1976, 105, 399-406.
34. Isolated dichlorophenylgold(III) (0.2 mmol) was reacted with 0.4 mmol of AgOTf and 0.4 mmol of n-butyl triflate at 120°C in dichloroethane. The reaction was monitored by GC/MS. The product yield was determined by GC peak intensity after comparing to that of the standard compound (Supporting Information Figure Sl).
35. Teiber, J. F.; Draganov, D. I.; La Du, B. N. Biochem. Pharmacol. 2003, 66, 887-896.
36. Kotsuki, H.; Oshisi, T.; Inoue, M. Synlett 1998, 255-256.