First Application of Secondary Phosphines as Supporting Ligands for the Palladium-Catalyzed Heck Reaction: Efficient Activation of Aryl Chlorides

Advanced Synthesis and Catalysis

Volumn 344, Issue 5, 2002, Pages 495-498

  Schnyder, Anita ^a   Aemmer, Thomas ^a   Indolese, Adriano F ^a   Pittelkow, Ulrich ^a   Studer, Martin ^a  

^a SOLVIAS AG   (Switzerland)

Author keywords

Arylation; C C coupling; Heck reaction; Palladium; Secondary phosphine

Indexed keywords

EID: 0344753867     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200207)344:5<495::AID-ADSC495>3.0.CO;2-6     Document Type: Article

References (35)

1. a) J. Tsuji, Palladium Reagents and Catalysts, John Wiley and Sons Ltd., Chichester, 1995;
2. b) G. Stark, T. H. Riermeier, M. Beller, Transition Metals for Organic Synthesis, Vol. 1, (eds:. M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, pp. 208;
3. c) A. De Meijere, F. E. Meyer, Angew. Chem. Int. Ed. Engl. 1994, 33, 2379;
4. d) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
5. For reviews, see: a) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301; b) R. Stürmer, Angew. Chem. Int. Ed. Engl. 1999, 38, 3307; c) H. Gröger, J. Prakt. Chem. 2000, 342, 334; d) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047.
6. For reviews, see: a) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301; b) R. Stürmer, Angew. Chem. Int. Ed. Engl. 1999, 38, 3307; c) H. Gröger, J. Prakt. Chem. 2000, 342, 334; d) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047.
7. For reviews, see: a) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301; b) R. Stürmer, Angew. Chem. Int. Ed. Engl. 1999, 38, 3307; c) H. Gröger, J. Prakt. Chem. 2000, 342, 334; d) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047.
8. For reviews, see: a) T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301; b) R. Stürmer, Angew. Chem. Int. Ed. Engl. 1999, 38, 3307; c) H. Gröger, J. Prakt. Chem. 2000, 342, 334; d) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047.
9. a) A. Ehrentraut, A. Zapf, M. Beller, Synlett 2000, 1589;
10. b) D. Morales-Morales, R. Redon, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619;
11. c) A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10;
12. d) K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123;
13. e) M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. Int. Ed. Engl. 1998, 37, 481;
14. f) M. Beller, A. Zapf, Synlett 1998, 792;
15. g) M. Portnoy, Y. Ben-David, I. Rousso, D. Milstein, Organometallics 1994, 13, 3465;
16. h) M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734;
17. i) Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995.
18. 2 was synthesized according to J. R. Goerlich, R. Schmutzler, Phosphorus, Sulfur, and Silicon 1995, 102, 211.
19. Personal communication for O. Rouher and A. Robertson, Cytec Chem. Co., Niagara Falls, Cananda.
20. a) M. Ostermeier, J. Prieß, G. Helmchen, Angew. Chem. Int. Ed. 2002, 41, 612.
21. b) H. Bahrmann, B. Fell J. Mol. Catal. 1980, 8, 329;
22. c) J. L. Van Winkle, Brit. Patent 1,191,815, 1970; Chem. Abstr. 1970, 73, P66020v;
23. d) J. L. Van Winkle, R. C. Morris, R. F. Mason, DE 1,909,620, 1969; Chem. Abstr. 1970, 72, P3033h.
24. a) J. Albert, J. M. Cadena, J. Granell, G. Muller, D. Panyella, C. Sanudo, Eur. J. Inorg. Chem. 2000, 1283;
25. b) V. V. Dunina, L. G. Kuz'mina, M. Yu. Kazakova, Yu. K. Grishin, Yu. A. Veits, E. I. Kazakova, Tetrahedron Asymmetry 1997, 8, 2537;
26. c) M. A. Zhuravel, N. S. Grewal, D S. Glueck, K.-C. Lam, A. L. Rheingold, Organometallics 2000, 19, 2882;
27. d) R. J. Forder, I. S. Mitchell, G. Reid, R. H. Simpson, Polyhedron 1994, 13, 2129;
28. e) P. Leoni, F. Marchetti, S. Papucci, M. Pasquali, J. Organomet. Chem. 2000, 593, 12.
29. a) E. Alonso, J. Fornies, C. Fortuno, A. Martin, G. M. Rosair, A. Welch, J. Inorg. Chem. 1997, 36, 4426;
30. b) R. Glaser, D. J. Kountz, R. D. Waid, J. C. Gallucci, D. W. Meek, J. Am. Chem. Soc. 1984, 106, 6324;
31. c) P. Leoni, S. Papucci, M. Pasquali, Inorg. Chim. Acta 1999, 284, 246;
32. d) P. Leoni, G. Pieri, M. Pasquali, J. Chem. Soc. Dalton Trans. 1998, 657, and references therein.
33. a) O. Herd, A. Hessler, M. Hingst, P. Machnitzki, M. Tepper, O. Stelzer Catal. Today 1998, 42, 413;
34. b) O. Herd, A. Hessler, M. Hingst, M. Tepper, O. Stelzer J. Organomet. Chem. 1996, 522, 69;
35. c) D. E. Bergreiter, Y.-S. Liu, S. Furyk, B. L. Case, Tetrahedron Lett. 1998, 39, 8799.