Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes and alkenes

Pure and Applied Chemistry

Volumn 80, Issue 5, 2008, Pages 1127-1134

  Satoh, Tetsuya ^a   Ueura, Kenji ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C coupling; C H bond cleavage; Iridium; Isocoumarin; Naphthalene; Oxidative coupling; Phthalide; Rhodium

Indexed keywords

EID: 44649094452     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200880051127     Document Type: Conference Paper

References (71)

1. nd ed., John Wiley, Chichester (2004);
2. nd ed., Wiley-VCH, Weinheim (2004);
3. (c) K. Fagnou, M. Lautens. Chem. Rev. 103, 169 (2003);
4. (d) I. P. Beletskaya, A. V. Cheprakov. Chem. Rev. 100, 3009 (2000).
5. (a) C. Jia, T. Kitamura, Y. Fujiwara. Acc. Chem. Res. 34, 633 (2001);
6. (b) Y. Fujiwara, I. Moritani, S. Danno, S. Teranishi. J. Am. Chem. Soc. 91, 7166 (1969).
7. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani. Nature 366, 529 (1993).
8. Reviews: (a) D. Alberico, M. E. Scott, M. Lautens. Chem. Rev. 107, 174 (2007);
9. (b) T. Satoh, M. Miura. Chem. Lett. 36, 200 (2007);
10. (c) T. Satoh, M. Miura. J. Synth. Org. Chem. 64, 1199 (2006);
11. (d) B. L. Conley, W. J. Tenn III, K. J. H. Young, S. K. Ganesh, S. K. Meier, V. R. Ziatdinov, O. Mironov, J. Oxgaard, J. Gonzales, W. A. Goddard III, R. A. Periana. J. Mol. Catal. A 251, 8 (2006);
12. (e) M. Miura, T. Satoh. In Handbook of C-H Transformations, G. Dyker (Ed.), Vol. 1, p. 223, Wiley-VCH, Weinheim (2005);
13. (f) M. Miura, T. Satoh. Top. Organomet. Chem. 14, 55 (2005);
14. (g) F. Kakiuchi, N. Chatani. Adv. Synth. Catal. 345, 1077 (2003);
15. (h) C.-H. Jun, C. W. Moon, D.-Y. Lee. Chem.-Eur. J. 8, 2622 (2002);
16. (i) V. Ritleng, C. Sirlin, M. Pfeffer. Chem. Rev. 102, 1731 (2002);
17. (j) M. Miura, M. Nomura. Top. Curr. Chem. 219, 211 (2002);
18. (k) F. Kakiuchi, S. Murai. Acc. Chem. Res. 35, 826 (2002);
19. (l) G. Dyker. Angew. Chem., Int. Ed. 38, 1698 (1999);
20. (m) F. Kakiuchi, F. Murai. Top. Organomet. Chem. 3, 47 (1999);
21. (n) A. E. Shilov, G. B. Shul'pin. Chem. Rev. 97, 2879 (1997).
22. (a) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura. J. Org. Chem. 63, 5211 (1998);
23. (b) M. Miura, T. Tsuda, T. Satoh, M. Nomura. Chem. Lett. 1103 (1997).
24. (a) C. Amatore, C. Cammoun, A. Jutand. Adv. Synth. Catal. 349, 292 (2007);
25. (b) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen. J. Am. Chem. Soc. 124, 1586 (2002).
26. E. Capita, J. M. Brown, A. Ricci. Chem. Commun. 1854 (2005).
27. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi. J. Am. Chem. Soc. 129, 7666 (2007).
28. Recently, Pd-catalyzed ipso-decarboxylative arylation and ortho-arylation of arene and heteroarene carboxylic acids were reported. ipso-Arylation: (a) L. J. Gooßen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, L. M. Levy. J. Am. Chem. Soc. 129, 4824 (2007);
29. (b) J.-M. Becht, C. Catala, C. Le Drian, A. Wagner. Org. Lett. 9, 1781 (2007);
30. (c) L. J. Gooßen, G. Deng, L. M. Levy. Science 313, 662 (2006);
31. (d) P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau. J. Am. Chem. Soc. 128, 11350 (2006);
32. (e) T. Okazawa, T. Satoh, M. Miura, M. Nomura. J. Am. Chem. Soc. 124, 5286 (2002);
33. ortho-Arylation: (f) H. A. Chiong, Q.-N. Pham, O. Daugulis. J. Am. Chem. Soc. 129, 9879 (2007);
34. (g) R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu. J. Am. Chem. Soc. 129, 3510 (2007).
35. For example, see: (a) R. Rossi, A. Carpita, F. Bellina, P. Stabile, L. Mannina. Tetrahedron 59, 2067 (2003);
36. (b) T. Yao, R. C. Larock. J. Org. Chem. 68, 5936 (2003);
37. (c) R. S. Mali, K. N. Babu. J. Org. Chem. 63, 2488 (1998) and refs. cited therein.
38. Pt-catalyzed lactone synthesis via C-H bond activation directed by a carboxyl group and oxidative cyclization has been reported: (a) J. M. Lee, S. Chang. Tetrahedron Lett. 47, 1375 (2006);
39. (b) B. D. Dangel, J. A. Johnson, D. Sames. J. Am. Chem. Soc. 123, 8149 (2001).
40. For recent reports concerning Pd-catalyzed synthesis of isocoumarins and phthalides, see: (a) H. B. Mereyala, G. Pathuri. Synthesis 2944 (2006);
41. (b) V. Subramanian, V. Rao Batchu, D. Barange, M. Pal. J. Org. Chem. 70, 4778 (2005);
42. (c) X. Wu, A. K. Mahalingam, Y. Wan, M. Alterman. Tetrahedron Lett. 45, 4635 (2004);
43. (d) Y. Lee, Y. Fujiwara, K. Ujita, M. Nagamoto, H. Ohta, I. Shimizu. Bull. Chem. Soc. Jpn. 74, 1437 (2001);
44. (e) R. C. Larock, M. J. Doty, X. Han. J. Org. Chem. 64, 8770 (1999);
45. (f) K. Orito, M. Miyazawa, R. Kanbayashi, M. Tokuda, H. Suginome. J. Org. Chem. 64, 6583 (1999);
46. (g) H.-Y. Liao, C.-H. Cheng. J. Org. Chem. 60, 3711 (1995);
47. (h) R. C. Larock, E. K. Yum, M. J. Doty, K. K. C. Sham. J. Org. Chem. 60, 3270 (1995).
48. S. S. Stahl. Angew. Chem., Int. Ed. 43, 3400 (2004) and refs. therein.
49. (a) T. Sugihara, T. Satoh, M. Miura. Tetrahedron Lett. 46, 8269 (2005);
50. (b) T. Sugihara, T. Satoh, M. Miura, M. Nomura. Adv. Synth. Catal. 346, 1765 (2004);
51. (c) T. Sugihara, T. Satoh, M. Miura, M. Nomura. Angew. Chem., Int. Ed. 42, 4672 (2003);
52. (d) T. Yasukawa, T. Satoh, M. Miura, M. Nomura. J. Am. Chem. Soc. 124, 12680 (2002);
53. (e) K. Oguma, M. Miura, T. Satoh, M. Nomura. J. Organomet. Chem. 648, 297 (2002);
54. (f) Y. Kametani, T. Satoh, M. Miura, M. Nomura. Tetrahedron Lett. 41, 2655 (2000);
55. (g) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura. J. Org. Chem. 61, 6941 (1996);
56. (h) K. Kokubo, M. Miura, M. Nomura. Organometallics 14, 4521 (1995).
57. For Rh-catalyzed nonchelation-assisted vinylation of unactivated aromatic compounds, see: (a) T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida. J. Catal. 206, 272 (2002);
58. (b) T. Matsumoto, H. Yoshida. Chem. Lett. 1064 (2000).
59. For examples of Rh-catalyzed aerobic oxidation, see: (a) A. K. Fazlur-Rahman, J.-C. Tsai, K. M. Nicholas. J. Chem. Soc., Chem. Commun. 1334 (1992);
60. (b) M. Bressan, A. Morvillo. Inorg. Chim. Acta 166, 177 (1989);
61. (c) H. Mimoun. Angew. Chem., Int. Ed. Engl. 21, 734 (1982);
62. (d) H. Mimoun, M. M. Perez-Machirant, I. Sérée de Roch. J. Am. Chem. Soc. 100, 5437 (1978).
63. 2: (a) G. M. Whitesides, W. J. Ehmann. J. Am. Chem. Soc. 92, 5625 (1970);
64. (b) W. Herwig, W. Metlesics, H. Zeiss. J. Am. Chem. Soc. 81, 6203 (1959);
65. X = I: (c) S. Kawasaki, T. Satoh, M. Miura, M. Nomura. J. Org. Chem. 68, 6836 (2003);
66. (d) G. Wu, A. L. Rheingold, S. L. Feib, R. F. Heck. Organometallics 6, 1941 (1987);
67. (e) T. Sakakibara, Y. Tanaka, T.-I. Yamasaki. Chem. Lett. 797 (1986);
68. X = COCl, see ref. [13d]: o-dihalobenzenes: (f) W. Huang, X. Zhou, K.-I. Kanno, T. Takahashi. Org. Lett. 6, 2429 (2004).
69. (a) K. Ueura, T. Satoh, M. Miura. J. Org. Chem. 72, 5362 (2007);
70. (b) K. Ueura, T. Satoh, M. Miura. Org. Lett. 9, 1407 (2007).
71. For stoichiometric ortho-rhodation of a Cp*Rh benzoate, see: J. M. Kisenyi, G. J. Sunley, J. A. Cabeza, A. J. Smith, H. Adams, N. J. Salt, P. M. Maitlis. J. Chem. Soc., Dalton Trans. 2459 (1987).