Palladium-Catalyzed Sixfold Alkenylation of Hexabromobenzene: An Interesting Case of Self-Organization

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 12, 1997, Pages 1289-1292

  Prinz, Peter ^a   Lansky, Annegret ^a   Haumann, Thomas ^b   Boese, Roland ^b   Noltemeyer, Matthias ^a   Knieriem, Burkhard ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b Inst F Anorganische Chem Univ E   (Germany)

Author keywords

Arenes; Homogeneous catalysis; Palladium

Indexed keywords

EID: 0030835484     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199712891     Document Type: Article

References (50)

1. H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704, and references therein.
2. H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704, and references therein.
3. a) E. Weber, F. Vögtle, Angew. Chem. 1979, 91, 813-837; Angew. Chem. Int. Ed. Engl. 1979, 18, 753-776;
4. a) E. Weber, F. Vögtle, Angew. Chem. 1979, 91, 813-837; Angew. Chem. Int. Ed. Engl. 1979, 18, 753-776;
5. b) D. D. MacNicol, J. J. McKendrick, D. R. Wilson. Chem. Soc. Rev. 1978, 7, 65-87;
6. c) U. Rosenthal, W. Schulz, J. Prakt. Chem. 1986, 328, 335-341;
7. d) K. Praefcke, B. Kohne, D. Singer, Angew. Chem. 1990, 102, 200-202; Angew. Chem. Int. Ed. Engl. 1990, 29, 177-179, and references therein.
8. d) K. Praefcke, B. Kohne, D. Singer, Angew. Chem. 1990, 102, 200-202; Angew. Chem. Int. Ed. Engl. 1990, 29, 177-179, and references therein.
9. D. Astruc, Acc. Chem. Res. 1986, 19, 377-383; Top. Curr. Chem. 1992, 160, 47-95.
10. D. Astruc, Acc. Chem. Res. 1986, 19, 377-383; Top. Curr. Chem. 1992, 160, 47-95.
11. a) R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271; Angew. Chem. Int. Ed. Engl. 1986, 25, 268-269;
12. a) R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271; Angew. Chem. Int. Ed. Engl. 1986, 25, 268-269;
13. b) R. Boese, J. R. Green, J. Mittendorf, D. L. Mahler, K. P. C. Vollhardt, ibid. 1992, 104, 1643-1645 and 1992, 31, 1643-1645.
14. b) R. Boese, J. R. Green, J. Mittendorf, D. L. Mahler, K. P. C. Vollhardt, ibid. 1992, 104, 1643-1645 and 1992, 31, 1643-1645.
15. S. Bräse, J. Rümper, K. Voigt, S. Albecq, G. Thurau, R. Villard, B. Waegell, A. de Meijere, Liebigs Ann. 1997, in press.
16. a) A. Lansky, Ph.D. thesis, Universität Göttingen, 1992;
17. b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
18. b) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
19. c) see also ref.[11] in: B. König, H. Zieg, P. Bubenitschek, P. G. Jones, Chem. Ber. 1994, 127, 1811-1813.
20. Up to threefold vicinal couplings of 1,2,3-trihaloarenes and even fourfold couplings with 1,2,4,5-tetrahaloarenes with styrenes have been achieved under Jeffery conditions [8]: a) A. Lansky, O. Reiser, A. de Meijere, Synlett 1990, 405-407; b) K. Voigt, A. Lansky, M. Noltemeyer, A. de Meijere, Liebigs Ann. 1996, 899-911. Such multiple couplings did not proceed under traditional Heck conditions: W. Tao, S. Nesbitt, R. F. Heck, J. Org. Chem. 1990, 55, 63-69.
21. Up to threefold vicinal couplings of 1,2,3-trihaloarenes and even fourfold couplings with 1,2,4,5-tetrahaloarenes with styrenes have been achieved under Jeffery conditions [8]: a) A. Lansky, O. Reiser, A. de Meijere, Synlett 1990, 405-407; b) K. Voigt, A. Lansky, M. Noltemeyer, A. de Meijere, Liebigs Ann. 1996, 899-911. Such multiple couplings did not proceed under traditional Heck conditions: W. Tao, S. Nesbitt, R. F. Heck, J. Org. Chem. 1990, 55, 63-69.
22. Up to threefold vicinal couplings of 1,2,3-trihaloarenes and even fourfold couplings with 1,2,4,5-tetrahaloarenes with styrenes have been achieved under Jeffery conditions [8]: a) A. Lansky, O. Reiser, A. de Meijere, Synlett 1990, 405-407; b) K. Voigt, A. Lansky, M. Noltemeyer, A. de Meijere, Liebigs Ann. 1996, 899-911. Such multiple couplings did not proceed under traditional Heck conditions: W. Tao, S. Nesbitt, R. F. Heck, J. Org. Chem. 1990, 55, 63-69.
23. a) T. Jeffery, Tetrahedron Lett. 1985, 26, 2667;
24. b) J. Chem. Soc. Chem. Commun. 1984, 1287-1289.
25. a) R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 1972, 37, 2320-2322;
26. b) R. F. Heck, Acc. Chem. Res. 1979, 12, 146-151;
27. c) Palladium Reagents in Organic Syntheses, Academic Press, London, 1985;
28. d) for recent reviews see ref. [6b] and S. Bräse, A. de Meijere in Cross Coupling Reactions (Eds.: F. Diederich, P. Stang), Wiley-VCH, Weinheim, 1997.
29. N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 866-867; recent review: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
30. N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 866-867; recent review: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
31. a) D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1979, 101, 4992-4998;
32. reviews: b) J. K. Stille, Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
33. reviews: b) J. K. Stille, Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
34. c) T. N. Mitchell, Synthesis 1992, 803-815.
35. a) The unsubstituted hexaethenylbenzene was prepared by conventional six-fold dehydrobromination of hexakis(1′-bromoethyl)benzene: C. Krüger, M. Yalpani, Chem. Ber. 1983, 116, 3359-3365. b) Hexaisopropenylbenzene was obtained in only 4% yield by cobalt-mediated trimerization of diisopropenylacetylene: E. M. Arnett, J. M. Bollinger, J. C. Sanda, J. Am. Chem. Soc. 1965, 87, 2050-2051.
36. a) The unsubstituted hexaethenylbenzene was prepared by conventional six-fold dehydrobromination of hexakis(1′-bromoethyl)benzene: C. Krüger, M. Yalpani, Chem. Ber. 1983, 116, 3359-3365. b) Hexaisopropenylbenzene was obtained in only 4% yield by cobalt-mediated trimerization of diisopropenylacetylene: E. M. Arnett, J. M. Bollinger, J. C. Sanda, J. Am. Chem. Soc. 1965, 87, 2050-2051.
37. Hexastyrylbenzene and substituted hexastyrylbenzenes were prepared starting from the threefold coupling product of 1,3,5-tribromo-2,4,6-trimethylbenzene and styrene: H. Meier, N. Hanold, H. Kalbitz, Synthesis 1997, 276.
38. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1972, 94, 4370-4371.
39. W. A. Hermann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
40. W. A. Hermann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
41. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158-163.
42. R. F. Cunico, F. J. Clayton, J. Org. Chem. 1976, 41, 1480-1482.
43. Good-quality crystals of 3a and 3d were obtained by letting ethanol slowly diffuse into a saturated solution of 3a in hexane and 3d in hexane/ethanol.
44. w(F) = 0.1040 [20]. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-100 015 and -100 016. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
45. SHELXTL-PLUS (Program System for Crystal Structure Solution and Refinement, Universität Göttingen).
46. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
47. W. R. Roth, Universität Bochum (Germany), personal communication. We are indebted to Professor Roth for carrying out the calculations with his MM2-ERW program.
48. J. M. Bollinger, J. J. Burke, E. M. Arnett, J. Org. Chem. 1966, 31, 1310.
49. The cyclic voltammogram was kindly measured by Prof. Dr. S. Bäuerle and Dipl.-Chem. M. Emge, Universität Ulm (Germany)
50. J. O. Howell, J. M. Goncalves, C. Amatore, L. Klansinc, R. M. Wightman, J. K. Kochi, J. Am. Chem. Soc. 1984, 106, 3968-3976.