An efficient carbonylation of aryl halides catalysed by palladium complexes with phosphite ligands in supercritical carbon dioxide

Abstract

The carbonylation of aryl halides catalysed by CO₂ soluble Pd complexes with trialkyl or triaryl phosphite ligands proceeds rapidly in scCO₂, in which the rate of the reaction is higher than those attained in solution phase reactions.

References

1. Recent reviews; (a) P. G. Jessop, T. Ikariya and R. Noyori, Science, 1995, 269, 1065; (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999, 99, 475.
2. (a) P. G. Jessop, T. Ikariya and R. Noyori, Organometallics, 1995, 14, 1510; (b) M. J. Burk, S. Feng, M. F. Gross and W. Tumas, J. Am. Chem. Soc., 1995, 117, 8277; (c) J.-L. Xiao, S. C. A. Nefkens, P. G. Jessop, T. Ikariya and R. Noyori, Tetrahedron Lett., 1996, 37, 2813; (d) S. Kainz, D. Koch and W. Leitner, Selective Reactions of Metal-Activated Molecules, ed. H. Werner and W. Schreier, Vieweg, Wiesbaden, 1998, pp. 151–156; (e) S. Buelow, P. Dell'Orco, D. K. Morita, D. Pesiri, E. Birnbaum, S. Borkowsky, S. Feng, L. Luan, D. Morgenstern and W. Tumas, Green Chemistry, ed. O. T. Anastas and T. C. Williamson, OUP, New York, 1998, pp. 265–285.
3. (a) J. W. Rathke, R. J. Klingler and T. R. Krause, Organometallics, 1991, 10, 1350; (b) S. Kainz, D. Koch, W. Baumann and W. Leitner, Angew. Chem., 1997, 109, 1699; Angew. Chem., Int. Ed. Engl., 1997, 36, 1628; (c) D. Koch and W. Leitner, J. Am. Chem. Soc., 1998, 120, 13 398; (d) D. R. Palo and C. Erkey, Ind. Eng. Chem. Res., 1998, 37, 4203; (e) I. Bach and D. J. Cole-Hamilton, Chem. Commun., 1998, 1463.
4. (a) P. G. Jessop, T. Ikariya and R. Noyori, Nature, 1994, 368, 231; (b) P. G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1996, 118, 344.
5. K. M. Dooley and F. C. Knopf, Ind. Eng. Chem. Res., 1987, 26, 1910; G. J. Suppes, R. N. Occhiogrosso and M. A. McHugh, Ind. Eng. Chem. Res., 1989, 28, 1152; P. Srinivas and M. Mukhopadhyay, Ind. Eng. Chem. Res., 1994, 33, 3118; X.-W. Wu, Y. Oshima and S. Koda, Chem. Lett., 1997, 1045; P. G. Jessop, Top. Catal., 1998, 5, 95; U. Kreher, S. Schebesta and D. Walther, Z. Anorg. Allg. Chem., 1998, 624, 602.
6. A. Cowell and J. K. Stille, J. Am. Chem. Soc., 1980, 102, 4193.
7. Y. Kayaki, I. Shimizu and A. Yamamoto, Bull. Chem. Soc. Jpn., 1997, 70, 1141.
8. The TON values obtained from 18 h reactions in toluene under otherwise identical conditions decrease in the order: P(OEt)₃ > PMe₃..
9. [PdCl₂{PPh₃}₂] complex is known to react with CO in in Et₃N containing alcohols to give several kinds of Pd carbonyls and PPh₃. M. Hidai, M. Kokura and Y. Uchida, J. Organomet. Chem., 1973, 52, 431.
10. [Pd(CO)₄] is known to be thermally unstable; J. H. Darling and J. S. Ogden, J. Chem. Soc., Dalton Trans., 1973, 1079.
11. A. F. Lagante, B. N. Hansen, T. J. Bruno and R. E. Sievers, Inorg. Chem., 1995, 34, 5781; Y. H. Lin, N. G. Smart and C. M. Wai, Trends Anal. Chem., 1995, 14, 123; A. V. Yazdi and E. J. Beckmann, Ind. Eng. Chem. Res., 1997, 36, 2368; R. P. Hughes and H. A. Trujillo, Organometallics, 1996, 15, 286; M. A. Carroll and A. B. Holmes, Chem. Commun., 1998, 1395; D. K. Morita, D. R. Pesiri, S. A. David, W. H. Glaze and W. Tumas, Chem. Commun., 1998, 1397.