Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic conditions

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2191-2194

  Mino, Takashi ^a   Shirae, Yoshiaki ^a   Sakamoto, Masami ^a   Fujita, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; HALOGEN COMPOUNDS; MOLECULAR STRUCTURE; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

LIGANDS; N-METHYL-N-PHENYLHYDROAZONE; PRECURSORS; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

NITROGEN COMPOUNDS;

BORONIC ACID DERIVATIVE; HALIDE; HYDRAZONE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; SUZUKI REACTION;

CATALYSIS; GLYOXAL; HYDRAZONES; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXYGEN; PALLADIUM;

EID: 15444367411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048107i     Document Type: Article

References (42)

1. For reviewes, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (e) Llord-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
2. For reviewes, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (e) Llord-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
3. For reviewes, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (e) Llord-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
4. For reviewes, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (e) Llord-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
5. For reviewes, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (e) Llord-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
6. For examples, see: (a) Patel, M.; Rodgers, J. D.; McHugh, R. J., Jr.; Johnson, B. L.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3217. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Terahedron Lett. 2001, 42, 7717. (c) Vaz, B.; Rosana, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Terahedron Lett. 2001, 42, 7409. (d) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (e) Wong, K.-T.; Huang, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
7. For examples, see: (a) Patel, M.; Rodgers, J. D.; McHugh, R. J., Jr.; Johnson, B. L.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3217. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Terahedron Lett. 2001, 42, 7717. (c) Vaz, B.; Rosana, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Terahedron Lett. 2001, 42, 7409. (d) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (e) Wong, K.-T.; Huang, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
8. For examples, see: (a) Patel, M.; Rodgers, J. D.; McHugh, R. J., Jr.; Johnson, B. L.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3217. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Terahedron Lett. 2001, 42, 7717. (c) Vaz, B.; Rosana, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Terahedron Lett. 2001, 42, 7409. (d) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (e) Wong, K.-T.; Huang, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
9. For examples, see: (a) Patel, M.; Rodgers, J. D.; McHugh, R. J., Jr.; Johnson, B. L.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3217. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Terahedron Lett. 2001, 42, 7717. (c) Vaz, B.; Rosana, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Terahedron Lett. 2001, 42, 7409. (d) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (e) Wong, K.-T.; Huang, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
10. For examples, see: (a) Patel, M.; Rodgers, J. D.; McHugh, R. J., Jr.; Johnson, B. L.; Cordova, B. C.; Klabe, R. M.; Bacheler, L. T.; Erickson-Viitanen, S.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3217. (b) Wang, W.; Xiong, C.; Yang, J.; Hruby, V. J. Terahedron Lett. 2001, 42, 7717. (c) Vaz, B.; Rosana, R.; Nieto, M.; Paniello, A. I.; de Lera, A. R. Terahedron Lett. 2001, 42, 7409. (d) Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125. (e) Wong, K.-T.; Huang, T. S.; Lin, Y.; Wu, C.-C.; Lee, G.-H.; Peng, S.-M.; Chou, C. H.; Su, Y. O. Org. Lett. 2002, 4, 513.
11. For examples, see: (a) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (b) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Erase, S.; Rubsam, F. Chem. Eur. J. 1999, 5, 2584. (c) Nicolaou, K. C.; Koumbis, A. E.; Takayanagi, M.; Natarajan, S.; Jain, N. P.; Bando, T.; Li, H.; Hughes, R. Chem. Eur. J. 1999, 5, 2622. (d) Kamikawa, K.; Watanabe, T.; Daimon, A.; Uemura, M. Tetrahedron 2000, 56, 2325.
12. For examples, see: (a) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (b) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Erase, S.; Rubsam, F. Chem. Eur. J. 1999, 5, 2584. (c) Nicolaou, K. C.; Koumbis, A. E.; Takayanagi, M.; Natarajan, S.; Jain, N. P.; Bando, T.; Li, H.; Hughes, R. Chem. Eur. J. 1999, 5, 2622. (d) Kamikawa, K.; Watanabe, T.; Daimon, A.; Uemura, M. Tetrahedron 2000, 56, 2325.
13. For examples, see: (a) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (b) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Erase, S.; Rubsam, F. Chem. Eur. J. 1999, 5, 2584. (c) Nicolaou, K. C.; Koumbis, A. E.; Takayanagi, M.; Natarajan, S.; Jain, N. P.; Bando, T.; Li, H.; Hughes, R. Chem. Eur. J. 1999, 5, 2622. (d) Kamikawa, K.; Watanabe, T.; Daimon, A.; Uemura, M. Tetrahedron 2000, 56, 2325.
14. For examples, see: (a) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965. (b) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Erase, S.; Rubsam, F. Chem. Eur. J. 1999, 5, 2584. (c) Nicolaou, K. C.; Koumbis, A. E.; Takayanagi, M.; Natarajan, S.; Jain, N. P.; Bando, T.; Li, H.; Hughes, R. Chem. Eur. J. 1999, 5, 2622. (d) Kamikawa, K.; Watanabe, T.; Daimon, A.; Uemura, M. Tetrahedron 2000, 56, 2325.
15. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
16. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
17. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1895, 34, 2371.
18. (b) Weskamp, T.; Bohm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348.
19. (c) Bohm, V. P. W.; Gstottmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186.
20. (d) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1909, 64, 3804.
21. (e) Zhang, C.; Trudell, M. L. Terahedron Lett. 2000, 41, 595.
22. (a) Weissan, H.; Milstein, D. Chem. Commun. 1999, 1901.
23. (b) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2001, 1540.
24. (a) Alonso, D. A.; Najera, C.; Pacheco, M. C. Org. Lett. 2000, 2, 1823.
25. (b) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
26. Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077.
27. Tao, B.; Boykin, D. W. Terahedron Lett. 2002, 43, 4955.
28. (a) Tao, B.; Boykin, D. W. J. Org. Chem. 2004, 69, 4330.
29. (b) Tao, B.; Boykin, D. W. Terahedron Lett. 2003, 44, 7993.
30. (a) Bombieri, G.; Caglioti, L.; Cattalini, L.; Forsellini, E.; Gasparrini, F.; Graziani, R.; Vigato, P. A. J. Chem. Soc., Chem. Commun. 1971, 1415.
31. (b) Maresca, L.; Natile, G.; Cattalini, L.; Gasparrini, F. J. Chem. Soc., Dalton Trans. 1975, 1602.
32. (c) Mino, T.; Imiya, W.; Yamashita, M. Synlett 1997, 583.
33. (d) Bacchi, A.; Carcelli, M.; Pelagatti, P.; Pelizzi, C.; Pelizzi, G.; Salati, C.; Sgarabotto, P. Inorg. Chim. Acta 1999, 295, 171.
34. (e) Mino, T.; Shiotsuki, M.; Yamamoto, N.; Suenaga, T.; Sakamoto, M.; Fujita, T.; Yamashita, M. J. Org. Chem. 2001, 66, 1795 and references therein.
35. Preliminary communication: Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett 2003, 882.
36. (a) Bolger, J. A.; Ferguson, G.; James, J. P.; Long, C.; McArdle, P.; Vos, J. G. J. Chem. Soc., Dalton Trans. 1993, 10, 1577.
37. (b) Bocelli, G.; Cantoni, A.; Tosi, G. Acta Crystallogr., Sect. C 1992, C48, 1041.
38. (c) Maresca, L.; Natile, G.; Cattalini, L.; Gasparrini, F. J. Chem. Soc., Dalton Trans. 1975, 15, 1601.
39. (d) Caglioti, L.; Cattalini, L.; Gasparrini, F.; Ghedini, M.; Paolucci, G.; Vigato, P. A. Inorg. Chim. Acta 1973, 7, 538.
40. (e) Cattalinis, L.; Gasparrini, F.; Maresca, L.; Natile, G. J. Chem. Soc., Chem. Commun. 1973, 11, 369.
41. (a) Sharma, S. D.; Pandhi, S. B. J. Org. Chem. 1990, 55, 2196.
42. (b) Tosi, G.; Cardellini, L.; Bocelli, G. Acta Crystallogr., Sect. B 1988, B44, 55.