Rhodium-catalyzed cross-coupling of organoboron compounds with vinyl acetate

Angewandte Chemie - International Edition

Volumn 48, Issue 39, 2009, Pages 7217-7220

  Yu, Jung Yi ^a   Kuwano, Ryoichi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Acetates; Boranes; Catalysis; Coupling; Cross ; Homogeneous; Rhodium

Indexed keywords

ACETATES; BORANES; CARBON-CARBON BOND FORMATION; CROSS-; CROSS-COUPLINGS; HOMOGENEOUS; ORGANOBORON COMPOUND; PALLADIUM CATALYST; RHODIUM CATALYSTS; RHODIUM-CATALYZED; VINYL ACETATES;

BORON COMPOUNDS; CATALYSIS; CATALYSTS; HYDRIDES; PALLADIUM; RHODIUM;

RHODIUM COMPOUNDS;

EID: 70349932085     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903146     Document Type: Article

References (60)

1. Books: a) Metal-Catalyzed Cross-Coupling Reactions, 2nd. ed., Vol.1-2 (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
2. b) Cross-Coupling Reactions. A. Practical Guide (Ed.: N. Miyaura), Springer, Berlin, 2002.
3. a) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374;
4. b) S. Saito, M. Sakai, N. Miyaura, Tetrahedron Lett. 1996,37,2993 ;
5. c) A. F. Littke, G. C. Fu, Angew. Chem. 1998,110, 3586;
6. Angew. Chem. Int. Ed. 1998, 37, 3387;
7. d) D. W. Old, I. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722.
8. a) W. J. Scott, G. T. Crisp, J. K. Stille, J. Am. Chem. Soc. 1984, 106, 4630;
9. b) A. Huth, I. Beetz, I. Schumann, Tetrahedron 1989, 45, 6679.
10. a) K. Takai, K. Oshima, H. Nozaki, Tetrahedron Lett. 1980, 21, 2531;
11. b)Y. Nan, Z. Yang, Tetrahedron Lett. 1999, 40, 3321;
12. c) M. A. Huffman, N. Yasuda, Synlett 1999, 471.
13. a) E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc. 1979, 101, 2246;
14. b) M. Tobisu, T. Shimasaki, N. Chatani, Angew. Chem. 2008,120, 4944;
15. Angew. Chem. Int. Ed. 2008, 47, 4866.
16. a) H. Okamura, M. Miura, H. Takei, Tetrahedron Lett. 1979,20, 43;
17. b) E. Wenkert, T. W. Ferreira, E. L. Michelotti, J. Chem. Soc. Chem. Commun. 1979, 637.
18. T. Hayashi, Y. Katsuro, M. Kumada, Tetrahedron Lett. 1980,21, 3915.
19. a) K. Kikukawa, K. Kono, F. Wada, T. Matsuda, J. Org. Chem. 1983, 48,1333;
20. b) S. Darses, T. Jeffery, J.-P. Genet, J.-L. Brayer, J.-P. Demoute, Tetrahedron Lett. 1996, 37, 3857.
21. a) E. Wenkert, A.-L. Han, C.-J. Jenny, J. Chem. Soc. Chem. Commun. 1988, 975;
22. b) S. B. Blakey, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 6046.
23. J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119,12376.
24. a) S. R. Dubbaka, P. Vogel, J. Am. Chem. Soc. 2003, 125, 15292;
25. b) S. R. Dubbaka, P. Vogel, Org. Lett. 2004, 6, 95.
26. T. Saeki, E.-C. Son, K. Tamao, Org. Lett. 2004, 6, 617.
27. J. Liu, M. J. Robins, Org. Lett. 2004, 6, 3421.
28. L. K. Hwang, Y. Na, J. Lee, Y. Do, S. Chang, Angew. Chem. 2005, 117, 6322;
29. Angew. Chem. Int. Ed. 2005, 44, 6166.
30. a) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, A. Yamamoto, J Am. Chem. Soc. 1980, 102, 3758;
31. b) H. Tatamidani, F. Kakiuchi, N. Chatani, Org. Lett. 2004, 6, 3597; Review:
32. c) A. Zapf, Angew. Chem. 2003, 115, 5552;
33. Angew Chem. Int. Ed. 2003, 42, 5394.
34. a) L. Del Valle, J. K. Stille, L. S. Hegedus, J .Org. Chem. 1990,55, 3019;
35. b) Y. Uozumi, H. Danjo, T. Hayashi, J. Org. Chem. 1999, 64, 3384;
36. c) D. Bouyssi, V. Gerusz, G. Balme, Eur. J. Org. Chem. 2002, 2445.
37. R. Kuwano, M. Yokogi, Chem. Commun. 2005, 5899.
38. a) B.-T. Guan, Y. Wang, R.-J. Li, D.-G Yu, Z.-J. Shi, J, Am. Chem. Soc. 2008, 130, 14468;
39. b) K. W. Quasdorf, X. Tian, N. K. Garg, J. Am. Chem. Soc. 2008, 130, 14422.
40. R.-J. Li, Y-Z. Li, X.-Y. Lu, J. Liu, B.-T. Guan, Z.-J. Shi, Angew. Chem. 2008, 120, 10278;
41. Angew. Chem. Int. Ed. 2008, 47,10124.
42. a) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S.-i. Kodama, J. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc. Jpn. 1976, 49,1958;
43. b) T. Hayashi, M. Tajika, K. Tamao, M. Kumada, J. Am. Chem. Soc. 1976, 95, 3718;
44. c) E. Negishi, N. Okukado, A. O. King, D. E. V. Horn, B. I. Spiegel, J. Am. Chem. Soc. 1978, 100, 2254.
45. a) D. Steinhuebel, J. M. Baxter, M. Palucki, I. W. Davies, J. Org. Chem. 2005, 70, 10124;
46. b) T. M. Gøgsig, L. S. Søbjerg, A. T. Lindhardt, K. L. Jensen, T. Skrydstrup, J. Org. Chem. 2008, 73, 3404;
47. c) C. M. So, C. P. Lau, A. S. C. Chan, F. Y. Kwong, J. Org. Chem. 2008, 73, 7731.
48. For examples of the catalytic carbon-carbon bond formation using alkenyl acetates as substrates, see : a) M. Amatore, C. Gosmini, J. Périchon, Eur. J. Org. Chem. 2005, 989;
49. b)Y. Matsuura, M. Tamura, T. Kochi, M. Sato, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007,129, 9858.
50. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
51. a) S. Komiya, J.-i. Suzuki, K. Miki, N. Kasai, Chem. Lett. 1987, 1287;
52. b) J. G. Planas, T. Marumo, Y. Ichikawa, M. Hirano, S. Komiya, J. Chem. Soc. Dalton Trans. 2000, 2613.
53. a) R. E. King III, D. C. Busby, M. F. Hawthorne, J. Organomet. Chem. 1985, 279, 103;
54. b) M. Murakami, H. Igawa, Helv. Chim. Acta 2002, 55, 4182.
55. a) M. Sasaki, H. Hayashi, N. Miyaura, Organometallics 1997,16, 4229;
56. b) T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002,124, 5052.
57. 4 (9% at 40 min, 100% at 8 h). (Z)-7 would have been detected in the GC analyses if the reaction of (E)-6 produced (Z)-7 directly.
58. During preparation of this manuscript, Larhed and co-workers reported a palladium-catalyzed Heck-type reaction of arylboronic acids with 2, see: J. Lindh, I Sävmarker, P. Nilsson, P. J. R. Sjöberg, M. Larhed, Chem. Eur. J 2009,15, 4630.
59. Arylboronates can be prepared by the catalytic C-H bond activation of arenes under halogen-free conditions: a) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr., M. R. Smith III, Science 2002, 295, 305;
60. b) T. Ishiyama, I. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, I. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390.