Palladium-catalyzed Ullmann-type coupling with zinc in the presence of H2O in liquid carbon dioxide

Green Chemistry

Volumn 4, Issue 5, 2002, Pages 424-425

  Li, Jinheng ^a   Xie, Yexiang ^a   Jiang, Huanfeng ^b   Chen, Mingcai ^b  

^a HUNAN NORMAL UNIVERSITY   (China)

^b GUANGZHOU INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57249092622     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b207096k     Document Type: Article

References (22)

1. (a) L. Jia, H. Jiang and J. Li, Green Chem., 1999, 1, 91;
2. (b) L. Jia, H. Jiang and J. Li, Chem. Commun., 1999, 985;
3. (c) J. Li and H. Jiang, Chem. Commun., 1999, 2369;
4. (d) J. Li, H. Jiang and M. Chen, Green Chem., 2001, 3, 137 and references cited therein
5. (e) G. Li, H. Jiang and J. Li, Green Chem., 2001, 3, 250;
6. (f) R. A. Brown, P. Pollet, E. Mckoon, C. A. Eckert, C. L. Liotta and P. G. Jessop, J. Am. Chem. Soc., 2001, 123, 1254 and references cited therein
7. (g) P. Munshi, A. D. Main, J. C. Linshan and P. G. Jessop, J. Am. Chem. Soc., 2002, 124, 7963.
8. For representative reviews, see: (a) Chemical Synthesis using Supercritical Fluids, eds. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999; (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999,99, 475; (c) J. Li, L. Jia and H. Jiang, Chinese J. Org. Chem., 2000, 20, 293; (d) R. S. Oakes, A. A. Clifford and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 2001, 917.
9. For representative reviews, see: (a) Chemical Synthesis using Supercritical Fluids, eds. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999; (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999,99, 475; (c) J. Li, L. Jia and H. Jiang, Chinese J. Org. Chem., 2000, 20, 293; (d) R. S. Oakes, A. A. Clifford and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 2001, 917.
10. For representative reviews, see: (a) Chemical Synthesis using Supercritical Fluids, eds. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999; (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999,99, 475; (c) J. Li, L. Jia and H. Jiang, Chinese J. Org. Chem., 2000, 20, 293; (d) R. S. Oakes, A. A. Clifford and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 2001, 917.
11. For representative reviews, see: (a) Chemical Synthesis using Supercritical Fluids, eds. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999; (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999,99, 475; (c) J. Li, L. Jia and H. Jiang, Chinese J. Org. Chem., 2000, 20, 293; (d) R. S. Oakes, A. A. Clifford and C. M. Rayner, J. Chem. Soc., Perkin Trans. 1, 2001, 917.
12. (a) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;
13. (b) S. Zhang, D. Zhang and L. S. Liebeskind, J. Org. Chem., 1997, 62, 2312 and references cited therein.
14. For Ni catalyzed Ullmann-type couplings, see: (a) K. Takagi, N. Hayama and K. Sasaki, Bull. Chem. Soc. Jpn., 1984, 57, 1887; (b) G. Meyer, Y. Rollin and J. Perichon,J. Organomet. Chem., 1987, 333, 263.
15. For Ni catalyzed Ullmann-type couplings, see: (a) K. Takagi, N. Hayama and K. Sasaki,Bull. Chem. Soc. Jpn., 1984, 57, 1887; (b) G. Meyer, Y. Rollin and J. Perichon,J. Organomet. Chem., 1987, 333, 263.
16. For Pd/C catalyzed Ullmann-type couplings using Zn and water as the reducing regent, see: (a) S. Ventrakaman and C. J. Li, Org. Lett., 1999,1, 1133; (b) S. Ventrakaman and C. J. Li,Tetrahedron Lett., 2000, 41, 4831 and references cited therein (c) S. Mukhopadhyay, G. Rothenberg, D. Gitis and Y. Sasson, Org. Lett., 2000,2, 211.
17. For Pd/C catalyzed Ullmann-type couplings using Zn and water as the reducing regent, see: (a) S. Ventrakaman and C. J. Li, Org. Lett., 1999, 1, 1133; (b) S. Ventrakaman and C. J. Li, Tetrahedron Lett., 2000, 41, 4831 and references cited therein (c) S. Mukhopadhyay, G. Rothenberg, D. Gitis and Y. Sasson, Org. Lett., 2000, 2, 211.
18. For Pd/C catalyzed Ullmann-type couplings using Zn and water as the reducing regent, see: (a) S. Ventrakaman and C. J. Li, Org. Lett., 1999, 1, 1133; (b) S. Ventrakaman and C. J. Li, Tetrahedron Lett., 2000, 41, 4831 and references cited therein (c) S. Mukhopadhyay, G. Rothenberg, D. Gitis and Y. Sasson, Org. Lett., 2000, 2, 211.
19. For Pd/C catalyzed Ullmann-type couplings using other reducing regents, see: formate salts as the reducing regents: (a) S. Mukhopadhyay, G. Rothenberg, D. Gitis, H. Wiener and Y. Sasson, J. Chem. Soc., Perkin Trans. 2, 1999, 2481; (b) Hydrogen gas as the reducing regents (c) S. Mukhopadhyay, G. Rothenberg, H. Wiener and Y. Sasson, Tetrahedron, 1999, 55, 14763 and references cited therein.
20. For Pd/C catalyzed Ullmann-type couplings using other reducing regents, see: formate salts as the reducing regents: (a) S. Mukhopadhyay, G. Rothenberg, D. Gitis, H. Wiener and Y. Sasson, J. Chem. Soc., Perkin Trans. 2, 1999, 2481; (b) Hydrogen gas as the reducing regents (c) S. Mukhopadhyay, G. Rothenberg, H. Wiener and Y. Sasson, Tetrahedron, 1999, 55, 14763 and references cited therein.
21. For Pd/C catalyzed Ullmann-type couplings using other reducing regents, see: formate salts as the reducing regents: (a) S. Mukhopadhyay, G. Rothenberg, D. Gitis, H. Wiener and Y. Sasson, J. Chem. Soc., Perkin Trans. 2, 1999, 2481; (b) Hydrogen gas as the reducing regents (c) S. Mukhopadhyay, G. Rothenberg, H. Wiener and Y. Sasson, Tetrahedron, 1999, 55, 14763 and references cited therein.
22. 6.