Palladium-catalyzed hiyama cross-couplings of aryl arenesulfonates with arylsilanes

Journal of the American Chemical Society

Volumn 130, Issue 37, 2008, Pages 12250-12251

  Zhang, Liang ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SILANE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; SCREENING; TEMPERATURE;

EID: 51949111764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804672m     Document Type: Article

References (42)

1. For selected examples, see: (a) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 10.
2. (b) Hiyama, T. J. Organomet. Chem. 2002, 653, 58.
3. (c) Denmark, S. E.; Baird, J. D. Chem. - Eur. J. 2006, 12, 4954.
4. (d) Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556.
5. (e) Ackermann, L.; Gschrei, C. J.; Althammer, A.; Riederer, M. Chem. Commun. 2006, 1419.
6. (f) Wolf, C.; Lerebours, R. Org. Lett. 2004, 6, 1147.
7. For some recent developments in Hiyama cross-coupling chemistry, see: (a) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835.
8. (b) Itami, K.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2001, 123, 5600. and references therein.
9. (c) Lee, J.-Y.; Fu, G. J. Am. Chem. Soc. 2003, 125, 5616.
10. (d) Clarke, M. L. Adv. Synth. Catal. 2005, 347, 303.
11. (e) Seganish, W. M.; Handy, C. J.; DeShong, P. J. Org. Chem. 2005, 70, 8948.
12. (f) Alacid, E.; Nájera, C. Adv. Synth. Catal. 2006, 348, 945.
13. (g) Denmark, S. E.; Butler, C. R. Org. Lett. 2006, 8, 63.
14. Onak, T. Organoborane Chemistry; Academic Press: New York, 1975.
15. For examples of Suzuki-Miyaura reactions, see: (a) Tang, Z.-Y.; Hu, Q.-S J. Am. Chem. Soc. 2004, 126, 3058.
16. (b) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
17. (c) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060.
18. (d) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531.
19. (e) Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
20. (f) Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479.
21. (g) Huffman, M. A.; Yasuda, N. Synlett 1999, 471.
22. (h) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447.
23. (i) Baxter, J. M.; Steinhuebel, D.; Palucki, M.; Davies, I. W. Org. Lett. 2005, 7, 215.
24. (j) Tang, Z. Y.; Hu, Q.-S. Adv. Synth. Catal. 2004, 346, 1635.
25. (k) Steinhuebel, D.; Baxter, J. M.; Palucki, M.; Davies, I. W. J. Org. Chem. 2005, 70, 10124.
26. (l) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910.
27. (m) Zhang, L.; Meng, T.; Wu, J. J. Org. Chem. 2007, 72, 9346.
28. For examples of Sonogashira coupling, see: (a) Fu, X.; Zhang, S.; Yin, J.; Schumacher, D. P Tetrahedron Lett. 2002, 43, 6673.
29. (b) Gelman, D.; Buchwald, S. L. Angew. Chem. 2003, 42, 5993.
30. Heck coupling: Fu, X.; Zhang, S.; Yin, J.; McAllister, T. L.; Jiang, S. A.; Tann, C.-H.; Thiruvengadam, T. K.; Zhang, F. Tetrahedron Lett. 2002, 43, 573.
31. Kumada coupling: (c) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
32. (d) Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364.
33. (e) Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457.
34. Iron-catalyzed coupling of alkyl Grignard reagents with ArOTs: (f) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
35. Stille couplings: (g) Badone, D.; Cecchi, R.; Guzzi, U. J. Org. Chem. 1992, 57, 6321.
36. (h) Nagatsugi, F.; Uemura, K.; Nakashima, S.; Minora, M.; Sasaki, S. Tetrahedron Lett. 1995, 36, 421.
37. (I) Schio, L.; Chatreaux, F.; Klich, M Tetrahedron Lett. 2000, 41, 1543.
38. Negishi-type reaction of arenesulfonates: Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
39. (a) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008,ASAP, DOI: 10.1021/ar800036s and references therein.
40. (b) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
41. (c) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
42. (d) Buchwald, S. L. Adv. Synth. Catal. 2004, 346, 1599.