Rhodium-catalyzed oxidative coupling between salicylaldehydes and internal alkynes with C-H bond cleavage to produce 2,3-disubstituted chromones

Chemistry - An Asian Journal

Volumn 3, Issue 5, 2008, Pages 881-886

  Shimizu, Masaki ^a   Tsurugi, Hayato ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C coupling; C H activation; Homogeneous catalysis; Oxidation; Rhodium

Indexed keywords

EID: 54849421586     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800037     Document Type: Article

References (63)

1. For reviews concerning the functionalization of C-H bonds, see: a) F. Kakiuchi, Top Organomet. Chem. 2007, 24, 1;
2. b) L. Ackermann, Top Organomet. Chem. 2007, 24, 35;
3. c) T. Satoh, M. Miura, Top Organomet. Chem. 2007, 24, 61;
4. d) D. Kalyani, M. S. Sanford, Top Organomet. Chem. 2007, 24, 85;
5. e) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
6. f) C.-H. Jun, E.-A. Jo, J.-W. Park, Eur. J. Org. Chem. 2007, 1869;
7. g) T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200;
8. h) T. Satoh, M. Miura, J. Synth. Org. Chem. Jpn. 2006, 64, 1199;
9. i) 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 2006, 251, 8;
10. j) M. Miura, T. Satoh in Handbook of C-H Transformations, Vol. 1 (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005, p. 223;
11. k)M. Miura, T. Satoh, Top Organomet. Chem. 2005, 14, 55;
12. l) M. S. Sigman, M. Schults, Org. Biomol. Chem. 2004, 2, 2551;
13. m) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077;
14. n) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
15. o) M. Miura, M. Nomura, Top. Curr. Chem. 2002, 219, 211;
16. p) F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826;
17. q) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
18. r) F. Kakiuchi, S. Murai, Top. Organomet. Chem. 1999, 3, 47;
19. s) G. Dyker, Angew. Chem. 1999, 111, 1808;
20. Angew. Chem. Int. Ed. 1999, 38, 1698;
21. t) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879.
22. a) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211;
23. b) M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. 1997, 1103.
24. a) K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362;
25. b) K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407.
26. For the Rh-catalyzed oxidative coupling of benzene with ethylene, see: a) T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Catal. 2002, 206, 272;
27. b) T. Matsumoto, H. Yoshida, Chem. Lett. 2000, 1064;
28. for the Rh-catalyzed oxidative arylation of 2-aryl pyridines and an imine, see: c) T. Vogler, A. Studer, Org. Lett. 2008, 10, 129;
29. for examples of rhodium-catalyzed aerobic oxidation, see: d) A. K. Fazlur-Rahman, J.-C. Tsai, K. M. Nicholas, J. Chem. Soc. Chem. Commun. 1992, 1334;
30. e) M. Bressan, A. Morvillo, Inorg. Chim. Acta 1989, 166, 177;
31. f) H. Mimoun, Angew. Chem. 1982, 94, 750;
32. Angew. Chem. Int. Ed. Engl. 1982, 21, 734;
33. g) H. Mimoun, M. M. Perez-Machirant, I. Sérée de Roch, J. Am. Chem. Soc. 1978, 100, 5437.
34. J . Tsuji, Palladium Reagents and Catalysts, 2nd ed., John Wiley & Sons, Chichester, 2004.
35. a) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Org. Chem. 1997, 62, 4564;
36. b) K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1999, 72, 303;
37. c) K. Oguma, M. Miura, T. Satoh, M. Nomura, J. Am. Chem. Soc. 2000, 122, 10464;
38. d) T. Sugihara, T. Satoh, M. Miura, M. Nomura, Adv. Synth. Catal. 2004, 346, 1765;
39. e) K. Ueura, T. Satoh, M. Miura, Org. Lett. 2005, 7, 2229;
40. f) T. Katagiri, H. Tsurugi, A. Funayama, T. Satoh, M. Miura, Chem. Lett. 2007, 36, 830;
41. g) T. Uto, M. Shimizu, K. Ueura, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 298.
42. For a Pd-catalyzed arylation, see: a) T. Satoh, T. Itaya, M. Miura, M. Nomura, Chem. Lett. 1996, 823;
43. for an Ir-catalyzed arylation, see: b) Y. Nishinaka, T. Satoh, M. Miura, H. Morisaka, M. Nomura, H. Matsui, C. Yamaguchi, Bull. Chem. Soc. Jpn. 2001, 74, 1727;
44. for Rh-catalyzed alkylation, see: c) M. Imai, M. Tanaka, S. Nagumo, N. Kawahara, H. Suemune, J. Org. Chem. 2007, 72, 2543, and references therein;
45. d) R. T. Stemmler, C. Bolm, Adv. Synth. Catal. 2007, 349, 1185.
46. See , for example: a) A. K. Soni, G. L. D. Krupadanam, G. Srimannarayana, Synth. Commun. 2007, 37, 795;
47. b) P. Valenti, A. Bisi, A. Rampa, F. Belluti, S. Gobbi, A. Zampiron, M. Carrara, Bioorg. Med. Chem. 2000, 8, 239;
48. c) A. LTvai, T. Patonay, Monatsh. Chem. 1995, 126, 219;
49. d) A. Saeed, A. P. Sharma, N. Durani, R. Jain, S. Durani, R. S. Kapil, J. Med. Chem. 1990, 33, 3210;
50. e) E. S. C. Wu, J. T. Loch III, B. H. Toder, A. R. Borrelli, D. Gawlak, L. A. Radov, N. P. Gensmantel, J. Med. Chem. 1992, 35, 3519.
51. a) M. I. Lvovskaya, A. D. Roshal, A. O. Doroshenko, A. V. Kyrychenko, V. P. Khilya, Spectrochim. Acta Part A 2006, 65, 397;
52. b) W. Sato, T. Nakai, T. Yoneyama, Mitsubishi Chemical Copr., Japan Japanese Patent JP 2004155665, 2004;
53. c) R. Schipfer, O. S. Wolfbeis, A. Knierzinger, J. Chem. Soc. Perkin Trans. 2 1981, 1443.
54. A similar promotional effect of this ligand was observed in the reaction of triaryl methanol compounds with alkynes; see reference [6g].
55. 3)], see: R. P. Hughes, D. C. Lindner, L. M. Liable-Sands, A. L. Rheingold, Organometallics 2001, 20, 3519.
56. I-catalyzed hydroacylation of the alkyne (see reference [6a,b]) is followed by oxidative cyclization, cannot be excluded. However, it is known that dialkyl acetylenes, such as 2g, undergo hydroacylation smoothly under RhI catalysis. Under the present oxidative conditions, 2g underwent sluggish coupling with 1a, and no hydroacylation product was formed in a detectable amount. Thus, the predominant active species in the present reaction seems to be different from that in the hydroacylation.
57. Z. Novák, P. Nemes, A. Kotschy, Org. Lett. 2004, 6, 4917.
58. S . S. Hirsch, W. J. Bailey, J. Org. Chem. 1978, 43, 4090.
59. T. C. Chadha, H. S. Mahal, K. Venkataraman, J. Chem. Soc. 1933, 1459.
60. A. Saeed, A. P. Sharma, N. Durani, R. Jain, S. Durani, R. S. Kapil, J. Med. Chem. 1990, 33, 3210.
61. G. Wittig, F. Bangert, H. E. Richter, Justus Liebigs Ann. Chem. 1925, 446, 155.
62. C. Pan, J. Yu, Y. Zhou, Z. Wang, M.-M. Zhou, Synlett 2006, 1657.
63. S . Gobbi, A. Cavalli, A. Rampa, F. Belluti, L. Piazzi, A. Paluszcak, R. W. Hartmann, M. Recanatini, A. Bisi, J. Med. Chem. 2006, 49, 4777.