Palladium-catalyzed carboacylation of alkenes by using acylchromates as acyl donors

Bulletin of the Chemical Society of Japan

Volumn 78, Issue 2, 2005, Pages 331-340

  Yamane, Motoki ^a   Kubota, Yuko ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; AROMATIC COMPOUNDS; CATALYSIS; CHROMATES; PALLADIUM; THERMAL EFFECTS;

ACYL DONORS; ACYLCHROMATES; ARYL IODIDE; CARBOACYLATION;

OLEFINS;

ALKENE; BENZENE; BENZOFURAN DERIVATIVE; CHROMIC ACID; INDOLE DERIVATIVE; IODIDE; KETONE; LIGAND; METAL COMPLEX; NORBORNENE DERIVATIVE; PALLADIUM; SOLVENT; TOLUENE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 14744306367     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.331     Document Type: Article

References (82)

1. For reviews, see: a) J. Tsuji, Acc. Chem. Res., 2, 144 (1969).
2. b) J. K. Stille, L. F. Fries, R. W. Fries, P. K. Wong, D. E. James, and K. S. Y. Lau, Adv. Chem. Ser., 57, 1799 (1974).
3. c) J. Tsuji, "Organic Synthesis with Palladium Compounds," Springer Verlag, Heidelberg (1980).
4. d) A. Yamamoto, T. Yamamoto, and F. Ozawa, Pure Appl. Chem., 57, 1799 (1985).
5. e) D. Milstein, Acc. Chem. Res., 21, 428 (1988).
6. f) E. Drent, Pure Appl. Chem., 62, 661 (1990).
7. a) T. Sato, K. Naruse, M. Enokiya, and T. Fujisawa, Chem. Lett., 1981, 1135.
8. b) J. J. Tufariello and G. B. Mullen, J. Am. Chem. Soc., 100, 3636 (1978).
9. c) C. S. Cho, K. Itotani, and S. Uemura, J. Organomet. Chem., 443, 253 (1993).
10. d) M. Haddach and J. R. McCarthy, Tetrahedron Lett., 40, 3109 (1999).
11. a) K. Oguma, M. Miura, T. Satoh, and M. Nomura, J. Organomet. Chem., 648, 297 (2002).
12. b) R. Kakino, S. Yasumi, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 75, 137 (2002).
13. c) R. Kakino, H. Narahashi, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 75, 1333 (2002).
14. d) L. J. Goossen, L. Winkel, A. Dohring, K. Ghosh, and J. Paetzold, Synlett, 8, 1237 (2002).
15. a) A. Zarf, Angew. Chem., Int. Ed., 42, 5394 (2003).
16. b) R. Kakino, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 74, 371 (2001).
17. c) H. Tatamidani, K. Yokota, F. Kakiuchi, and N. Chatani, J. Org. Chem., 69, 5615 (2004).
18. d) T. Hirai, H. Kuniyasu, T. Kato, Y. Kurata, and N. Kambe, Org. Lett., 5, 3871 (2003).
19. a) C. F. Lochow and R. G. Miller, J. Am. Chem. Soc., 98, 1281 (1976).
20. b) K. Tanaka and G. C. Fu, J. Am. Chem. Soc., 123, 11492 (2001).
21. c) K. Sakai, J. Ide, O. Oda, and N. Nakamura, Tetrahedron Lett., 13, 1287 (1972).
22. d) M. Tanaka, K. Sakai, and H. Suemune, Curr. Org. Chem., 7, 353 (2003).
23. e) R. C. Larock, K. Oertle, and G. F. Potterr, J. Am. Chem. Soc., 102, 190 (1980).
24. f) Y. Sato, Y. Oonishi, and M. Mori, Angew. Chem., Int. Ed., 41, 1218 (2002).
25. g) M. Miura and M. Nomura, J. Synth. Org. Chem., Jpn., 58, 578 (2000).
26. h) K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura, Bull. Chem. Soc. Jpn., 72, 303 (1999), and references therein.
27. a) E. Shirakawa, Y. Nakao, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 122, 9030 (2000).
28. b) E. Shirakawa, K. Yamasaki, H. Yoshida, and T. Hiyama, J. Am. Chem. Soc., 121, 10221 (1999).
29. c) R. Hua, S.-Y. Onozawa, and M. Tanaka, Organometallics, 19, 3269 (2000).
30. a) M. Tanaka, Tetrahedron Lett., 28, 2601 (1979).
31. b) I. Ojima, Z. Zhang, A. Korda, P. Ingallina, and N. Clos, "New Science in Homogenious Transition Metal Catalyzed Reactions," ed by W. R. Moser, Advances in Chemistry Series, American Chemical Society, Washington, DC (1992), Chap. 19, pp. 277-296.
32. M. Kosugi, H. Naka, and T. Migita, Chem. Lett., 1987, 1371.
33. T. Koga, S. Makinouchi, and N. Okukado, Chem. Lett., 1988, 1141.
34. a) Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 39, 6249 (1998).
35. b) Y. Hanzawa, N. Tabuchi, K. Saito, S. Noguchi, and T. Taguchi, Angew. Chem., Int. Ed., 38, 2395 (1999).
36. c) Y. Hanzawa and T. Taguchi, J. Synth. Org. Chem., Jpn., 62, 314 (2004), and references therein.
37. a) Y. Obora, Y. Ogawa, Y. Imai, T. Kawamura, and Y. Tsuji, J. Am. Chem. Soc., 123, 10489 (2001).
38. b) M. Yamane, T. Amemiya, and K. Narasaka, Chem. Lett., 2001, 1210.
39. a) H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 1999, 309.
40. b) M. Yamane, Y. Ishibashi, H. Sakurai, and K. Narasaka, Chem. Lett., 2000, 174.
41. c) H. Sakurai, K. Tanabe, and K. Narasaka, Chem. Lett., 2000, 168.
42. E. O. Fischer and A. Massböl, Chem. Ber., 100, 2445 (1967).
43. M. Yamane, Y. Kubota, and K. Narasaka, Phosphorus, Sulfur Silicon Relat. Elem., 177, 2105 (2002).
44. a) R. P. Hughes and J. Powell, J. Organomet. Chem., 60, 409 (1973).
45. b) R. R. Stevens, J. Organomet. Chem., 21, 495 (1970).
46. c) E. Ban, R. Hughes, and J. Powell, J. Organomet. Chem., 69, 455 (1974).
47. d) R. P. Hughes and J. Powell, J. Organomet. Chem., 34, C51 (1972).
48. e) R. P. Hughes and J. Powell, J. Chem. Soc., Chem. Commun., 1971, 275.
49. f) R. C. Larock, S. Varaprath, H. H. Lau, and C. A. Fellows, J. Am. Chem. Soc., 106, 5274 (1984).
50. g) D. Medema, R. Helden, and C. F. Kohll, Inorg. Chim. Acta, 3, 255 (1969); R. Helden, C. F. Kohll, D. Medema, G. Verberg, and T. Jonkhoff, Recl. Trav. Chim. Pays-Bas, 90, 324 (1971).
51. g) D. Medema, R. Helden, and C. F. Kohll, Inorg. Chim. Acta, 3, 255 (1969); R. Helden, C. F. Kohll, D. Medema, G. Verberg, and T. Jonkhoff, Recl. Trav. Chim. Pays-Bas, 90, 324 (1971).
52. h) Y. Yamamoto, M. Al-Masum, and N. Asao, J. Am. Chem. Soc., 116, 6019 (1994).
53. i) B. Trost and G. Kottirsch, J. Am. Chem. Soc., 112, 2816 (1990).
54. j) A. Ogawa, J. Kawakami, N. Sonoda, and T. Hirao, J. Org. Chem., 61, 4161 (1996).
55. k) I. Shimizu and J. Tsuji, Chem. Lett., 1984, 233.
56. l) R. C. Larock, Y. He, W. W. Leong, X. Han, M. D. Refvik, and J. M. Zenner, J. Org. Chem., 63, 2154 (1998).
57. J. Hine, G. Louis, and C. L. Liotta, J. Org. Chem., 32, 2600 (1967).
58. a) E. Negishi, T. Nguyen, B. O'Connor, J. M. Evans, and A. Silveira, Heterocycles, 28, 55 (1989).
59. b) R. C. Larock and D. E. Stinn, Tetrahedron Lett., 29, 4687 (1988).
60. a) R. Odle, B. Blevins, M. Ratcliff, and L. S. Hegedus, J. Org. Chem., 45, 2709 (1980).
61. b) R. C. Larock and S. Babu, Tetrahedron Lett., 28, 5291 (1987).
62. c) A. E. S. Gelpke, J. J. N. Veerman, M. S. Goedheijt, P. C. J. Kamer, P. W. N. M. van Leeuwen, and H. Hiemstra, Tetrahedron, 55, 6657 (1999).
63. G. Stork and K. Zhao, Tetrahedron Lett., 30, 2173 (1989).
64. E. Negishi, T. Nguyen, B. O'Connor, J. M. Evans, and A. Silveire, Heterocycles, 28, 55 (1989).
65. A. Casaschi, R. Grigg, and J. M. Sansano, Tetrahedron, 57, 607 (2001).
66. R. Grigg, J. M. Sansano, V. Santhakumar, V. Sridharan, R. Thangavelanthum, M. Thornton-Pett, and D. Wilson, Tetrahedron, 53, 11803 (1997).
67. R. Odle, B. Blevins, M. Ratcliff, and L. S. Hegedus, J. Org. Chem., 45, 2709 (1980).
68. G. A. Molander and L. S. Harring, J. Org. Chem., 55, 6171 (1990).
69. R. F. Heck, J. Am. Chem. Soc., 90, 5546 (1968).
70. K. Suzuki, H. Kitagawa, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 66, 3729 (1993).
71. T. Saeki, E.-C. Son, and K. Tamao, Org. Lett., 6, 617 (2004).
72. C. Zhou and R. C. Larock, J. Am. Chem. Soc., 126, 2303 (2004).
73. G. A. Olah, N. Friedman, J. Lukas, and J. M. Bollinger, J. Am. Chem. Soc., 88, 5328 (1966).
74. L. Syper, Tetrahedron Lett., 37, 4493 (1966).
75. C. H. Heathcock, L. G. Gulick, and T. Dehlinger, J. Heterocycl. Chem., 6, 141 (1969).
76. T. Mukaiyama, K. Takahashi, and I. Kuwajima, Bull. Chem. Soc. Jpn., 41, 1491 (1968).
77. G. H. Posner, D. J. Brunelle, and L. Sinoway, Synthesis, 1974, 662.
78. P. L. Couturier, Ann. Chim., 10, 559 (1983).
79. J. A. Nieman and M. D. Ennis, J. Org. Chem., 66, 2175 (2001).
80. D. Nagarathnam, J. Heterocycl. Chem., 29, 953 (1992).
81. Y. Kikugawa, Synthesis, 1981, 461.
82. T. Naito and I. Ninomiya, Synthesis, 1989, 778.