Pd(II)-catalyzed C-H activation/aryl-aryl coupling of phenol esters

Journal of the American Chemical Society

Volumn 132, Issue 2, 2010, Pages 468-469

  Xiao, Bin ^a   Fu, Yao ^a   Xu, Jun ^a   Gong, Tian Jun ^a   Dai, Jian Jun ^a   Yi, Jun ^a   Liu, Lei ^b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; CHEMICAL EQUATIONS; CYCLOPALLADATION; CYCLOPALLADATION REACTION; PHENOL DERIVATIVES; PHENOL ESTERS;

ESTERIFICATION; ESTERS; OXYGEN; PALLADIUM; PALLADIUM COMPOUNDS; PHENOLS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

COORDINATION REACTIONS;

PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; X RAY ANALYSIS;

EID: 74949097467     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909818n     Document Type: Article

References (42)

1. Recent reviews: (a) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
2. (b) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
3. (c) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.; Lazareva, A. Synlett 2006, 3382.
4. (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
5. (b) Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156.
6. (c) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
7. (d) Li, B.; Tian, S.; Fang, Z.; Shi, Z. Angew. Chem., Int. Ed. 2008, 47, 1115.
8. (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
9. (b) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
10. (c) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.
11. (d) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882.
12. (a) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
13. (b) Desai, L.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
14. (c) Thu, H.; Yu, W.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
15. Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266.
16. (a) Lazareva, A.; Daugulis, O. Org. Lett. 2006, 8, 5211.
17. (b) Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666.
18. (c) Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
19. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
20. (a) Horino, H.; Inoue, N. J. Org. Chem. 1981, 46, 4416.
21. (b) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
22. (a) Hennings, D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
23. (b) Hennings, D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379.
24. (a) Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851.
25. (b) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407.
26. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
27. (d) Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
28. (a) Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676.
29. (b) Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
30. (c) Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215.
31. (d) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510.
32. (a) For an example of Pd(0)-catalyzed ortho arylation of benzaldehydes with ArBr under nonoxidative conditions, see: Gürbüz, N.; Ö zdemir, I.; Ç etinkaya, B. Tetrahedron Lett. 2005, 46, 2273.
33. (b) For the use of phenol carbamates, see: Bedford, R. B.; Webster, R. L.; Mitchell, C. J. Org. Biol. Chem. 2009, 7, 4853.
34. (a) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
35. (b) Oi, S.; Watanabe, S.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003, 44, 8665.
36. 2O in the crystal may come from moisture in the reaction. For a related example, see: (a) Ball, N. D.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 3796.
37. (a) Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610.
38. (b) Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521.
39. Million, M.-E.; Boiziau, J.; Parker, F.; Tocque, B.; Roques, B. P.; Garbay, C. J. Med. Chem. 1995, 38, 4693.
40. (a) Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.
41. (b) Guo, Q.-X.; Liu, H.; Guo, C.; Luo, S.-W.; Gu, Y.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 3790.
42. (c) Schaus, S. E.; McDougal, N. T. J. Am. Chem. Soc. 2003, 125, 12094.