A New Catalyst System for the Heck Reaction of Unreactive Aryl Halides

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 481-483

  Reetz, Manfred T ^a   Lohmer, Gunther ^a   Schwickardi, Renate ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

C C coupling; Heck reaction; Homogeneous catalysis; Palladium; Regioselectivity

Indexed keywords

EID: 0032473435     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<481::aid-anie481>3.3.co;2-9     Document Type: Article

References (38)

1. Reviews of Heck reactions: a) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985; b) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995; c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
2. Reviews of Heck reactions: a) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985; b) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995; c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
3. Reviews of Heck reactions: a) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985; b) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995; c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
4. Reviews of Heck reactions: a) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985; b) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995; c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
5. Reviews of Heck reactions: a) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985; b) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995; c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2;
6. e) T. Jeftery, Adv. Met.-Org. Chem. 1996, 5, 153.
7. B. Cornils, W. A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996.
8. a) W. A. Hermann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844;
9. a) W. A. Hermann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844;
10. b) W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357.
11. a) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047;
12. b) Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995;
13. c) M. T. Reetz, G. Lohmer, Chem. Commun. 1996, 1921;
14. d) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091.
15. M. T. Reetz, G. Lohmer, R. Schwickardi, DE-A 19712388.0, 1997.
16. 4PCl (relative to Pd) are employed.
17. 4PCl (45.0 mg, 0.12 mmol), degassed three times under vacuum, and then flushed with argon. Anhydrous sodium acetate (164.0 mg, 2.0 mmol), chlorobenzene (1a; 112.6 mg, 1.0 mmol) and styrene (2: 130.2 mg, 1.25 mmol) were added. Following the addition of 1 mL NMP (or DMF) the flask was closed, and the contents stirred for 30 min at 120°C and then 12 h at 150°C After the usual workup, the mixture was analyzed by gas chromatography. The reaction was performed analogously with N,N-dimethylglycine (DMG) as additive.
18. M. Sakamoto, I. Shimizu, A. Yamamoto, Chem. Lett. 1995, 1101.
19. a) Y. Hirusawa, M. Oku, K. Yamamoto, Bull. Chem. Soc. Jpn. 1957, 30, 667;
20. b) L. Horner, G. Mummenthey, H. Moser, P. Beck, Chem. Ber. 1966, 99, 2782;
21. c) C. B. Ziegler, R. F. Heck, J. Org. Chem. 1978, 43, 2941;
22. d) T. Migita, T. Nagai, K. Kiuchi, M. Kosugi, Bull. Chem. Soc. Jpn. 1983, 56, 2869;
23. e) L. Cassar, M. Foà, J. Organomet. Chem. 1974, 74, 75.
24. Various anionic Pd-species have been postulated as possible intermediates in Heck reactions: [1] a) W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033; b) C. Amatore, A. Jutand, M. A. M'Barki, Organometallics 1992, 11, 3009;
25. Various anionic Pd-species have been postulated as possible intermediates in Heck reactions: [1] a) W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033; b) C. Amatore, A. Jutand, M. A. M'Barki, Organometallics 1992, 11, 3009;
26. c) E. Negishi, T. Takahashi, K. Akiyoshi, J. Chem. Soc. Chem. Commun. 1986, 1338.
27. n].
28. n].
29. n].
30. a) D. Hellwinkel, Top. Curr. Chem. 1983, 109, 1.
31. b) We thank Prof. Hellwinkel for a sample of 6b. Compound 6a was prepared by ion exchange.
32. 2X as arylating agents are common: [1] a) K.-C. Kong, C.-H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313; b) D. K. Monta, J. K. Stille, J. R. Norton, ibid. 1995, 117, 8576; c) W. A. Herrmann, C. Brossmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal. A: Chem. 1995, 103, 133.
33. 2X as arylating agents are common: [1] a) K.-C. Kong, C.-H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313; b) D. K. Monta, J. K. Stille, J. R. Norton, ibid. 1995, 117, 8576; c) W. A. Herrmann, C. Brossmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal. A: Chem. 1995, 103, 133.
34. 2X as arylating agents are common: [1] a) K.-C. Kong, C.-H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313; b) D. K. Monta, J. K. Stille, J. R. Norton, ibid. 1995, 117, 8576; c) W. A. Herrmann, C. Brossmer, K. Öfele, M. Beller, H. Fischer, J. Mol. Catal. A: Chem. 1995, 103, 133.
35. 2-catalyzed reaction of bromo° benzene (1b) with styrene (2) and other olefins, the nature of the base and the phosphane affects regioselectivity: S. Klingelhöfer, C. Schellenberg, J. Pommerehne, H. Bässler, A. Greiner, W. Heitz, Macromol. Chem. Phys. 1997, 198, 1511.
36. M. Beller, A. Tafesh, W. A. Herrmann (Hoechst AG), EP 725049 A1, 1996 [Chem. Abstr. 1996, 125, 221376].
37. M. Beller, A. Tafesh, W. A. Herrmann (Hoechst AG), EP 725049 A1, 1996 [Chem. Abstr. 1996, 125, 221376].
38. 4NBr was added (Jeffery conditions[1e]).[3]