Xantphos as an efficient ligand for palladium-catalyzed cross-coupling reactions of aryl bromides and triflates with allyl acetates and indium

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 1165-1168

  Seomoon, Dong ^a   Phil, Ho Lee ^a  

^a Kangwon National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ACETATES; ARYL BROMIDES; CROSS-COUPLING REACTIONS; TRIFLATES;

CATALYST ACTIVITY; FUNCTIONAL GROUPS; INDIUM; LIGANDS; PALLADIUM;

PHOSPHORUS COMPOUNDS;

ACETIC ACID DERIVATIVE; BROMIDE; INDIUM; LIGAND; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; XANTPHOS;

ALLYLATION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 38849083358     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702279t     Document Type: Article

References (39)

1. (a) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G., Abel, E. W., Eds.; Pergamon: Oxford, UK, 1982; Vol. 8, pp 799-938.
2. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
3. (c) Farina, V. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G., Abel, E. W., Eds.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 161-240.
4. (d) Tsuji, J. Palladium Reagents and Catalyst; Wiley: Chichester, UK, 1995; Chapter 4.
5. (e) Metal-Catalyzed Cross-Couplings Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
6. (f) Malleron, J.; Fiaud, J.; Legros, J. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: San Diego, CA, 1997.
7. (g) Negishi, E. Organopalladium Chemistry; Wiley-Interscience: New York, 2002; Vols. I and II.
8. (a) Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201-3204.
9. (b) Lee, K.; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265-8268.
10. (a) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
11. (b) Cintas, P. Synlett 1995, 1087-1096.
12. (c) Li, C.-J. Tetrahedron 1996, 52, 5643-5668.
13. (d) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
14. (e) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149-11176.
15. (f) Babu, G.; Perumal, P. T. Aldrichim. Acta 2000, 33, 16-22.
16. (g) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015-3020.
17. (h) Pae, A. N.; Cho, Y. S. Curr. Org. Chem. 2002, 6, 715-737.
18. (i) Podlech, J.; Maier, T. C. Synthesis 2003, 633-655.
19. (j) Li, C.-J. Chem. Rev. 2005, 105, 3095.
20. (a) Araki, S.; Kamei, T.; Hirashita, T.; Yamamura, H.; Kawai, M. Org. Lett. 2000, 2, 847-849.
21. (b) Jang, T.-S.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Synthesis 2003, 775-779.
22. (c) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745-6751.
23. (d) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2004, 69, 1415-1418.
24. (e) Hirashita, T.; Kambe, S.; Tsuji, H.; Omori, H.; Araki, S. J. Org. Chem. 2004, 69, 5054-5059.
25. (f) Nguyen, V. C.; Kim, Y.-T.; Yu, Y.-K.; Kang, H.-Y. Bull. Korean Chem. Soc. 2005, 26, 711-712.
26. (a) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901-3903.
27. (b) Lee, P. H.; Sung, S.-Y.; Lee, K.; Chang, S. Synlett 2002, 146-148.
28. (c) Lee, P. H.; Lee, S. W.; Lee, K. Org. Lett. 2003, 5, 1103-1106.
29. (d) Lee, P. H.; Lee, S. W.; Seomoon, D, Org. Lett. 2003, 5, 4963-4966.
30. (e) Lee, S. W.; Lee, K.; Seomoon, D.; Kim, S.; Kim, H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Lee, P. H. J. Org. Chem. 2004, 69, 4852-4855.
31. (f) Lee, P. H.; Lee, K. Angew. Chem., Int. Ed. 2005, 44, 3253-3256.
32. (g) Lee, P. H.; Seomoon, D.; Lee, K. Org. Lett. 2005, 7, 343-345.
33. (h) Lee, P. H.; Shim, E.;, Lee, K.; Seomoon, D.; Kim, S. Bull. Korean Chem. Soc. 2005, 26, 157-160.
34. (i) Lee, P. H.; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006, 128, 1139-1146.
35. (a) Lee, P. H.; Seomoon, D.; Lee, K.; Kim, S.; Kim. H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Sridhar, M. Adv. Synth. Catal. 2004, 346, 1641-1645.
36. (b) Seomoon, D.; Lee, K.; Kim, H.; Lee, P. H. Chem. Eur. J. 2007, 13, 5197-5206.
37. (a) Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 3081-3089.
38. (b) van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741-2769.
39. (c) Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Acc. Chem. Res. 2001, 34, 895-904.