Palladium(II)-catalyzed Michael-type hydroarylation of nitroalkenes using aryltins and sodium tetraarylborates

Bulletin of the Chemical Society of Japan

Volumn 76, Issue 7, 2003, Pages 1423-1431

  Ohe, Toshiyuki ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYSIS; LITHIUM COMPOUNDS; PALLADIUM;

HYDROARYLATION;

OLEFINS;

ACETIC ACID; ALKENE DERIVATIVE; BISMUTH DERIVATIVE; BORATE SODIUM; CALCIUM CHLORIDE; LEWIS ACID; LITHIUM CHLORIDE; MAGNESIUM CHLORIDE; PALLADIUM; TIN CHLORIDE; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION;

EID: 0041660637     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.1423     Document Type: Article

References (64)

1. a) C. S. Cho, K. Itotani, and S. Uemura, J. Organomet. Chem., 443, 253 (1993).
2. b) C. S. Cho, S. Motofusa, and S. Uemura, Tetrahedron Lett., 35, 1739 (1994).
3. c) C. S. Cho, S. Motofusa, K. Ohe, S. Uemura, and S. C. Shim, J. Org. Chem., 60, 883 (1995).
4. d) C. S. Cho and S. Uemura, J. Organomet. Chem., 465, 85 (1994).
5. e) C. S. Cho, T. Ohe, and S. Uemura, J. Organomet. Chem., 496, 221 (1995).
6. T. Ohe, T. Wakita, S. Motofusa, C. S. Cho, K. Ohe, and S. Uemura, Bull. Chem. Soc. Jpn., 73, 2149 (2000).
7. a) C. S. Cho, K. Tanabe, and S. Uemura, Tetrahedron Lett., 35, 1275 (1994).
8. b) C. S. Cho, S. Motofusa, K. Ohe, and S. Uemura, Bull. Chem. Soc. Jpn., 69, 2341 (1996).
9. c) C. S. Cho, K. Tanabe, O. Itoh, and S. Uemura, J. Org. Chem., 60, 274 (1995).
10. d) K. Matoba, S. Motofusa, C. S. Cho, K. Ohe, and S. Uemura, J. Organomet. Chem., 574, 3 (1999).
11. Examples of transition metal-catalyzed or -mediated Michael-type conjugate addition to nitroalkenes using organoheteroatom compounds, a) Organoboronic acids-Rh(I) (catalyzed), T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc., 122, 10716 (2000). b) Dialkylzinc-Cu(II) (catalyzed), A. Alexakis and C. Benhaim, Org. Lett., 2, 2579 (2000); S. Ongeri, U. Piarulli, R. F. W. Jackson, and C. Gennari, Eur. J. Org. Chem., 2001, 803; C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 124, 8192 (2002). c) Aryl iodide-Pd (mediated), S. E. Denmark and M. E. Schnute, J. Org. Chem., 60, 1013 (1995).
12. Examples of transition metal-catalyzed or -mediated Michael-type conjugate addition to nitroalkenes using organoheteroatom compounds, a) Organoboronic acids-Rh(I) (catalyzed), T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc., 122, 10716 (2000). b) Dialkylzinc-Cu(II) (catalyzed), A. Alexakis and C. Benhaim, Org. Lett., 2, 2579 (2000); S. Ongeri, U. Piarulli, R. F. W. Jackson, and C. Gennari, Eur. J. Org. Chem., 2001, 803; C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 124, 8192 (2002). c) Aryl iodide-Pd (mediated), S. E. Denmark and M. E. Schnute, J. Org. Chem., 60, 1013 (1995).
13. Examples of transition metal-catalyzed or -mediated Michael-type conjugate addition to nitroalkenes using organoheteroatom compounds, a) Organoboronic acids-Rh(I) (catalyzed), T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc., 122, 10716 (2000). b) Dialkylzinc-Cu(II) (catalyzed), A. Alexakis and C. Benhaim, Org. Lett., 2, 2579 (2000); S. Ongeri, U. Piarulli, R. F. W. Jackson, and C. Gennari, Eur. J. Org. Chem., 2001, 803; C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 124, 8192 (2002). c) Aryl iodide-Pd (mediated), S. E. Denmark and M. E. Schnute, J. Org. Chem., 60, 1013 (1995).
14. Examples of transition metal-catalyzed or -mediated Michael-type conjugate addition to nitroalkenes using organoheteroatom compounds, a) Organoboronic acids-Rh(I) (catalyzed), T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc., 122, 10716 (2000). b) Dialkylzinc-Cu(II) (catalyzed), A. Alexakis and C. Benhaim, Org. Lett., 2, 2579 (2000); S. Ongeri, U. Piarulli, R. F. W. Jackson, and C. Gennari, Eur. J. Org. Chem., 2001, 803; C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 124, 8192 (2002). c) Aryl iodide-Pd (mediated), S. E. Denmark and M. E. Schnute, J. Org. Chem., 60, 1013 (1995).
15. Examples of transition metal-catalyzed or -mediated Michael-type conjugate addition to nitroalkenes using organoheteroatom compounds, a) Organoboronic acids-Rh(I) (catalyzed), T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc., 122, 10716 (2000). b) Dialkylzinc-Cu(II) (catalyzed), A. Alexakis and C. Benhaim, Org. Lett., 2, 2579 (2000); S. Ongeri, U. Piarulli, R. F. W. Jackson, and C. Gennari, Eur. J. Org. Chem., 2001, 803; C. A. Luchaco-Cullis and A. H. Hoveyda, J. Am. Chem. Soc., 124, 8192 (2002). c) Aryl iodide-Pd (mediated), S. E. Denmark and M. E. Schnute, J. Org. Chem., 60, 1013 (1995).
16. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
17. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. b) S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. c) G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. d) A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, e) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, f) I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
18. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. b) S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. c) G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. d) A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, e) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, f) I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
19. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. b) S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. c) G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. d) A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, e) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, f) I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
20. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. b) S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. c) G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. d) A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, e) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, f) I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
21. Recent examples of atom economical reactions: Organotin compounds, a) K. Fugami, S. Ohnuma, M. Kameyama, T. Saotome, and M. Kosugi, Synlett, 1999, 63. b) S. Kobayashi, K. Sugita, and H. Oyamada, Synlett, 1999, 138. c) G. Harada, M. Yoshida, and M. Iyoda, Chem. Lett., 2000, 160. d) A. McCluskey, I. W. Muderawan, Muntari, and D. J. Young, J. Org. Chem., 66, 7811 (2001). Organoboron compounds, e) N. A. Bumagin and D. N. Korolev, Tetrahedron Lett., 40, 3057 (1999). Organoindium compounds, f) I. Pérez, J. P. Sestelo, and L. A. Sarandeces, Org. Lett., 1, 1267 (1999).
22. Preliminary results have already been reported in the form of a communication: T. Ohe and S. Uemura, Tetrahedron Lett., 43, 1269 (2002).
23. 2 in place of organotin compounds.
24. 3 showed only a low catalytic activity.
25. "Organobismuth Chemistry," ed by H. Suzuki and Y. Matano, Elsevier, London (2001), Chap. 5.
26. In the presence of a base such as NaOAc, Pd(II) catalyst is considered to be reduced to zero valent Pd to which the carbon-heteroatom bond (i.e., C-B bond) adds oxidatively to produce an organopalladium(II) species. Actually, Pd(O) complex also worked effectively as a catalyst in these reactions. On the contrary, the present catalytic system does not contain any base, and Pd(II) itself seems to work for transmetallation to afford the organopalladium(II) species. In fact, we observed that the reaction stopped when a black Pd(O) species appeared during the hydroarylation.
27. M. Sakai, H. Hayashi, and N. Miyaura, Organometallics, 16, 4229 (1997).
28. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
29. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
30. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
31. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
32. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
33. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
34. 4NF, d) E. Fouquet, M. Pereyle, and A. L. Rodriguez, J. Org. Chem., 62, 5242 (1997). e) E. Fouquet and A. L. Rodriguez, Synlett, 1997, 1323. f) A. L. Rodriguez, G. Peron, C. Duprat, M. Vallier, E. Fouquet, and F. Fages, Tetrahedron Lett., 39, 1179 (1998). g) E. Fouquet, M. Pereyre, A. L. Rodriguez, and T. Roulet, Bull. Soc. Chim. Fr., 134, 959 (1997). See also Ref. 5a.
35. For example, D. E. Worrall, Org. Synth., Coll. Vol. I, 413 (1941).
36. a) J. R. Doyle, P. E. Slade, and H. B. Jonassen, Inorg. Synth., 6, 218 (1960).
37. b) M. R. Kharasch, R. C. Seyler, and F. R. Mayo, J. Am. Chem. Soc., 60, 882 (1938).
38. c) S. Uemura, A. Spencer, and G. Wilkinson, J. Chem. Soc., Dalton Trans., 1973, 2565, and references therein.
39. For example: a) M. Kira, "Shin-Jikken Kagaku Koza," Vol. 12, ed by H. Sakurai, Maruzen, Tokyo (1965), p. 395.
40. b) P. Pfeiffer and K. Schunurnann, Ber. Dtsch. Chem. Ges., 37, 319 (1904).
41. c) R. K. Ingham, S. D. Rosenberg, and H. Gilman, Chem. Rev., 60, 459 (1960).
42. T. Ohe, T. Tanaka, M. Kuroda, C. S. Cho, K. Ohe, and S. Uemura, Bull. Chem. Soc. Jpn., 72, 1851 (1999).
43. J. R. Desmurs, M. Labrouillère, C. Le Roux, H. Gaspard, A. Laporterie, and J. Dubac, Tetrahedron Lett., 38, 8871 (1997).
44. S. Venkatraman, Y. Meng, and C.-J. Li, Tetrahedron Lett., 42, 4459 (2001).
45. D. E. Worrall, J. Am. Chem. Soc., 60, 2841 (1938).
46. H. L. Goebel and H. H. Wenzke, J. Am. Chem. Soc., 60, 697 (1938).
47. W. Ried and M. Wilk, Angew. Chem., 65, 398 (1953).
48. E. Knoevnagel and L. Walter, Ber. Dtsch. Chem. Ges., 37, 4505 (1904).
49. M. J. Kamlet, J. Am. Chem. Soc., 77, 4896 (1955).
50. K. W. Rosenmund, Ber. Dtsch. Chem. Ges., 42, 4778 (1909).
51. F. G. P. Remfly, J. Chem. Soc., 99, 286 (1911).
52. N. Campbell, W. Anderson, and J. Gilmore, J. Chem. Soc., 1940, 446.
53. A. C. Huitric and W. D. Kumler, J. Am. Chem. Soc., 78, 614 (1956).
54. X. A. Dominguez, J. Shim, and A. Elizondo, J. Am. Chem. Soc., 75, 4581 (1953).
55. F. I. Carrol, J. D. White, and M. E. Wall, J. Org. Chem., 28, 1236 (1963).
56. S. E. Demmark and L. R. Marcin, J. Org. Chem., 58, 3850 (1993).
57. P. Knochel and D. Seebach, Synthesis, 1982, 1017.
58. R. F. Cunico, J. Org. Chem., 55, 4474 (1990).
59. R. D. Grant, J. T. Pinhey, E. Rizzardo, and G. C. Smith, Aust. J. Chem., 38, 1505 (1985).
60. G. Ya. Vanag, V. I. Platpiere, and M. A. Matskanova, Zh. Obshch. Khim., 19, 1535 (1949); Chem. Abstr., 44, 1087d (1950).
61. G. Ya. Vanag, V. I. Platpiere, and M. A. Matskanova, Zh. Obshch. Khim., 19, 1535 (1949); Chem. Abstr., 44, 1087d (1950).
62. H. B. Hass, M. B. Neher, and R. T. Blickenstaff, Ind. Eng. Chem., 43, 2875 (1951); Chem. Abstr., 46, 5556e (1952).
63. H. B. Hass, M. B. Neher, and R. T. Blickenstaff, Ind. Eng. Chem., 43, 2875 (1951); Chem. Abstr., 46, 5556e (1952).
64. 2CuZnCl], which was made from t-butyllithium, zinc chloride, and copper(I) iodide, to β-nitrostyrene in THF. An example of conjugate addition using zinc organocuprates to nitroalkenes, H. P. Knoess, M. T. Furlong, M. J. Rozema, and P. Knochel, J. Org. Chem., 56, 5974 (1991).