Tuning the Selectivity of Heterogeneous Catalysts: A Trimetallic Approach to Reductive Coupling of Chloroarenes in Water

Advanced Synthesis and Catalysis

Volumn 343, Issue 3, 2001, Pages 274-278

  Mukhopadhyay, Sudip ^a   Rothenberg, Gadi ^b   Sasson, Yoel ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF YORK   (United Kingdom)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Bismuth; C C coupling; Chloroarenes; Heterogeneous catalysis; Palladium; Trimetallic catalysis

Indexed keywords

EID: 0001555056     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010330)343:3<274::AID-ADSC274>3.0.CO;2-P     Document Type: Article

References (27)

1. For a review, see J. H. Clark, D. J. Macquarrie, Org. Process Res. Dev. 1997, 1, 149.
2. (a) R. A. Sheldon, Chem. Ind. 1997, 12;
3. (b) R. A. Sheldon, J. Chem. Tech. Biotechnol. 1997, 68, 381.
4. For reviews on biaryl preparation methods and applications, see: (a) G. Bringmann, R. Walter, R. Weirich, Angew. Chem., Int. Ed. Engl. 1990, 29, 977;
5. (b) M. Sainsbury, Tetrahedron 1980, 36, 3327.
6. For a review, see: P. E. Fanta, Synthesis 1974, 9.
7. F. Ullmann, Ber. dtsch. chem. Ges. 1903, 36, 2389.
8. (a) D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205;
9. (b) J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793;
10. (c) for a combined homogeneous-heterogeneous approach, see: S. Mukhopadhyay, G. Rothenberg, D. Gitis, Y. Sasson, J. Org. Chem. 2000, 65, 3107.
11. (a) S. Mukhopadhyay, G. Rothenberg, H. Wiener, Y. Sasson, Tetrahedron 1999, 55, 14763;
12. (b) S. Mukhopadhyay, G. Rothenberg, D. Gitis, H. Wiener, Y. Sasson, J. Chem. Soc., Perkin Trans. 2 1999, 2481;
13. (c) S. Mukhopadhyay, G. Rothenberg, H. Wiener, Y. Sasson, New J. Chem. 2000, 24, 305;
14. (d) S. Mukhopadhyay, G. Rothenberg, D. Gitis, Y. Sasson, Org. Lett. 2000, 2, 211;
15. (e) for a critical discussion of this system, see also: J. A. Marshall, Chemtracts: Org. Chem. 2000, 265.
16. [7d]). Doth of these options, however, were impractical for large-scale synthesis.
17. S. Mukhopadhyay, G. Rothenberg, D. Gitis, M. Baidossi, D. E. Ponde, Y. Sasson, J. Chem. Soc., Perkin Trans. 2 2000, 1809.
18. (a) R. Ohnishi, W.-L. Wang, M. Ichikawa, Appl. Catal. (A) 1994, 113, 29;
19. (b) for a review, see: H. Van Bekkum, H. Roeper, F. Voragen, Carbohydr. Org. Raw Mater. III Workshop, Verlag Chemie: Weinheim, 1996, pp. 37-65.
20. In fact, this same combination of Pd, Pt and Bi on activated carbon was employed also for the elective oxidation of glucose to gluconic acid, cf. K. Deller, B. Despeyroux, in Catalysis of Organic Reactions (W.E. Pascoe, Ed.), Marcel Dekker: New York, NY, 1992; pp. 261-265; see also K. Deller, H. Krause, E. Peldszus, B. Despeyroux, German Patent DE 3823301, 1989 (to Degussa AG).
21. In fact, this same combination of Pd, Pt and Bi on activated carbon was employed also for the elective oxidation of glucose to gluconic acid, cf. K. Deller, B. Despeyroux, in Catalysis of Organic Reactions (W.E. Pascoe, Ed.), Marcel Dekker: New York, NY, 1992; pp. 261-265; see also K. Deller, H. Krause, E. Peldszus, B. Despeyroux, German Patent DE 3823301, 1989 (to Degussa AG).
22. N. Korte, L. Liang, R. Muftikian, C. Grittini, Q. Fernando, Platinum Metals Rev. 1997, 41, 2.
23. O. Levenspiel, Chemical Reaction Engineering; 2nd. edn., Wiley: New York, NY, 1972; pp. 238-239.
24. (a) To ensure that reaction rates were not mass transfer controlled, agitation speed was varied from 400 to 1000 rpm. Above 900 rpm, no increase in conversion was detected. All measurements hence pertain to 950 rpm stirring; (b) for reactions at different PhCl concentrations, xylene was added to make up the volume of the organic phase.
25. [7].
26. K. K. Park, C. H. Oh, W.-J. Sim, J. Org. Chem. 1995, 60, 6202.
27. Cf. M. Selva, C. A. Marques, P. Tundo, J. Org. Chem. 1994, 59, 3830.