Six- and eightfold palladium-catalyzed gross-coupling reactions of hexa- and octabromoarenes

Chemistry - A European Journal

Volumn 11, Issue 1, 2005, Pages 308-320

  Stulgies, Balder ^a   Prinz, Peter ^a   Magull, Jörg ^a   Rauch, Karsten ^a   Meindl, Kathrin ^a   Rühl, Stephan ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alkynes; Bromoarenes; Cross coupling; Palladium

Indexed keywords

ALKENYLBORONATES; ALKENYLSTANNANES; GROSS-COUPLING REACTIONS; HYDROBORATION;

BENZENE; CATALYSIS; CRYSTAL STRUCTURE; DERIVATIVES; KETONES; PALLADIUM; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

1 (TRIMETHYLSILYL)ETHYNYLCYCLOPROPANE; 1 ETHYNYL 1 METHYLCYCLOHEXANE; 1 ETHYNYL 1 METHYLCYCLOPROPANE; 1 ETHYNYLADAMANTANE; 2,3,6,7,10,11 HEXABROMOTRIPHENYLENE; 3,3 DIMETHYLPENTYNE; ALKENYL GROUP; AROMATIC COMPOUND; BENZENE DERIVATIVE; BORON DERIVATIVE; BROMINE; CYCLOHEXANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; HEXABROMOBENZENE; HEXAKIS(3,3 DIMETHYL 1 BUTENYL)TRIPHENYLENE; HEXAKIS(TERT BUTYLETHYL)BENZENE; PALLADIUM; PERBROMOARENE; POLYCYCLIC AROMATIC HYDROCARBON; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 19944426813     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400723     Document Type: Article

References (102)

1. a) B. Kohne, K. Praefcke, Chimia 1987, 41, 196-198;
2. b) K. Praefcke, B. Kohne, D. Singer, Angew. Chem. 1990, 102, 200-202; Angew. Chem. Int. Ed. Engl. 1990, 29, 177-179;
3. b) K. Praefcke, B. Kohne, D. Singer, Angew. Chem. 1990, 102, 200-202; Angew. Chem. Int. Ed. Engl. 1990, 29, 177-179;
4. c) S. Kuraar, S. Kumar Varshney, Angew. Chem. 2000, 772, 3270-3272; Angew. Chem. Int. Ed. 2000, 39, 3140-3142.
5. c) S. Kuraar, S. Kumar Varshney, Angew. Chem. 2000, 772, 3270-3272; Angew. Chem. Int. Ed. 2000, 39, 3140-3142.
6. a) K. Kondo, S. Yasuda, T. Sakaguchi, M. Miya, J. Chem. Soc. Chem. Commun. 1995, 55-56;
7. b) H. Meier, N. Hanold, H. Kalbitz, Synthesis 1997, 276-278.
8. B. Kayser, J. Altman, W. Beck, Chem. Eur. J. 1999, 5, 754-758.
9. O. Mongin, N. Hoyler, A. Gossauer, Eur. J. Org. Chem. 2000, 1193-1197.
10. a) D. D. MacNicol, G. A. Downing in Comprehensive Supramolecular Chemistry, Vol. 6 (Eds.: J. L. Atwood, J. E. D. Davis, D. D. Mac-Nicol, F. Vögtle, J.-M. Lehn), Pergaraon, Oxford, 1996, pp. 421-464;
11. b) D. D. MacNicol, D. R. Wilson, J. Chem. Soc. Chem. Commun. 1976, 494-495;
12. c) A. H. M. Elwahy, Tetrahedron Lett. 2001, 42, 5123-5126, and references therein.
13. a) D. Astruc, Acc. Chem. Res. 1986, 79, 377-383;
14. b) D. Astruc, Top. Curr. Chem. 1992, 160, 47-95;
15. c) D. Astruc, Acc. Chem. Res. 2000, 33, 287-298;
16. d) H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704.
17. d) H.-W. Marx, F. Moulines, T. Wagner, D. Astruc, Angew. Chem. 1996, 108, 1842-1845; Angew. Chem. Int. Ed. Engl. 1996, 35, 1701-1704.
18. a) R. Dierks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271; Angew. Chem. Int. Ed. Engl. 1986, 25, 268-269;
19. a) R. Dierks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271; Angew. Chem. Int. Ed. Engl. 1986, 25, 268-269;
20. b) R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, Angew. Chem. 1992, 104, 1643-1645; Angew. Chem. Int. Ed. Engl. 1992, 31, 1643-1645.
21. b) R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, Angew. Chem. 1992, 104, 1643-1645; Angew. Chem. Int. Ed. Engl. 1992, 31, 1643-1645.
22. a) K. Sonogashira in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P.J. Stang), Wiley-VCH, Weinheim, 1998, pp. 203-229;
23. b) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470.
24. a) S. Bräse, A. de Meijere in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004, pp. 217-315;
25. b) A. de Meijere, F. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
26. b) A. de Meijere, F. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
27. c) A. de Meijere, S. Erase, J. Organomet. Chem. 1999, 570, 88-100;
28. d) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
29. a) T. Jeffery, Tetrahedron Lett. 1985, 26, 2667-2670;
30. b) T. Jeffery, J. Chem. Soc. Chem. Commun. 1984, 1287-1289;
31. c) T. Jeffery, J.-Ch. Galland, Tetrahedron Lett. 1994, 35, 4103-4106.
32. Such cyclizations have indeed been observed in the coupling reactions of o-bromostyrenes with alkenes especially under Jeffery conditions; compare, S. Erase, J. Ruraper, K. Voigt, S. Albecq, G. Thurau, R. Villard, B. Waegell, A. de Meijere, Eur. J. Org. Chem. 1998, 671-678.
33. A. Lansky, Dissertation, Universität Göttingen, 1992.
34. a) N. Miyaura in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004, pp. 41-123;
35. b) A. R. Martin, Y. H. Yang, Acta Chem. Scand. 1993, 47, 221-230;
36. c) G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, T. R. Verhoeven, J. Org. Chem. 1994, 59, 8151-8156;
37. d) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
38. e) A. Suzuki in Perspectives in Organopalladium Chemistry for the XXI-Century (Ed.: J. Tsuji), Elsevier, Lausanne, 1999, pp. 147-168;
39. f) N. Miyaura, Top. Curr. Chem. 2002, 279, 11-59.
40. a) V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652;
41. b) T. N. Mitchell in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 167-202.
42. a) H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1972, 94, 4370-4371;
43. b) H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249-5255;
44. c) C. F. Lane, G. W. Kabalka, Tetrahedron 1976, 32, 981-990.
45. C. E. Tucker, J. Davidson, P. Knochel, J. Org. Chem. 1992, 57, 3482-3485.
46. B. Stulgies, Dissertation, Universität Göttingen 2001.
47. a) H Stetter, P. Goebel, Chem. Ber. 1962, 95, 1039-1042;
48. b) P. A. Bartlett, F. R. Green, E. H. Rose, J. Am. Chem. Soc. 1978, 700, 4852-4858.
49. a) E.-i. Negishi, A. O. King, J. M. Tour, Org. Synth. 1985, 64, 44-49;
50. b) E.-i Negishi, A. O. King, W. L. Klima, J. Org. Chem. 1980, 45, 2526-2528.
51. H.-C. Militzer, S. Schomenauer, C. Otte, C. Puls, J. Hain, S. Bräse, A. de Meijere, Synthesis 1993, 998-1012.
52. This methylation of (trimethylsilylethynyl)cyclopropane was first carried out by O. Eremenko in Göttingen; compare, J. Hellwig, Dissertation, Universität Göttingen 1999.
53. A. P. Meshcheryakov, L. V. Petrova, Uv. Akad. Nauk Gruz. SSR Ser. Khim. 1964, 1391-1398.
54. E. Rank, R. Bruckner, Eur. J. Org. Chem. 1998, 1045-1053.
55. J. A. Miller, M. C. Coleman, R. S. Matthews, J. Org. Chem. 1993, 58, 2637-2639.
56. G. F. Hennion, A. P. Boisselle, J. Org. Chem. 1961, 26, 725-726.
57. O. K. Behrens, J. Corse, D. E. Huff, R. G. Jones, Q. F. Soper, C. W. Whitehead, J. Biol. Chem. 1948, 775, 771-792.
58. A. J. Leusink, H. A. Budding, J. Organomet. Chem. 1968, 11, 533-539.
59. J. W. Labadie, J. K. Stille, J. Am. Chem. Soc. 1983, 105, 6129-6137.
60. P. Prinz, Dissertation, Universität Göttingen, 1996.
61. Preliminary communications: a) P. Prinz, A. Lansky, T. Haumann, R. Boese, M. Noltemeyer, B. Knieriem, A. de Meijere, Angew. Chem. 1997, 109, 1343-1346; Angew. Chem. Int. Ed. Engl. 1997, 36, 1289-1292;
62. Preliminary communications: a) P. Prinz, A. Lansky, T. Haumann, R. Boese, M. Noltemeyer, B. Knieriem, A. de Meijere, Angew. Chem. 1997, 109, 1343-1346; Angew. Chem. Int. Ed. Engl. 1997, 36, 1289-1292;
63. b) A. de Meijere, P. von Zezschwitz, H. N̈ske, B. Stulgies, J. Organomet. Chem. 2002, 653, 129-140.
64. a) S. W. Wright, D. L. Hagemann, L. D. McClure, J. Org. Chem. 1994. 59, 6095-6097;
65. b) S. T. Buchwald, J. M. Fox in Recent Progress in the Suzuki Reactions of Aryl Chlorides, The Strem Chemiker XVIII, Newburyport, 2000.
66. a) A. Suzuki, Pure Appl. Chem. 1994, 66, 213-222;
67. b) N. Miyaura in Advances in Metal-Organic Chemistry, Vol. 6 (Ed.: L. S. Liebeskind), Jai Press, London, 1998, pp. 187-243.
68. V. V. Grushin, H. Alper, Organometallics 1993, 12, 1890-1901.
69. a) W. A. Herrmann, C. Broßmer, K. Öfele, C-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 707, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1846;
70. a) W. A. Herrmann, C. Broßmer, K. Öfele, C-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 707, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1846;
71. b) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, Angew. Chem. 1995. 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1846-1849.
72. b) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, Angew. Chem. 1995. 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1846-1849.
73. M. Moreno-Manas, M. Ferez, R. Pleixats, J. Org. Chem. 1996, 61, 2346-2351.
74. J. Feng, G. Szeimies, Tetrahedron 2000, 56, 4249-4252.
75. V Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905-5911.
76. CCDC-100016 (1a), -100015 (1i), -182212 (1h), -100015 (23) and - 244 483 (27) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallo-graphic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)1223-336033; or email: deposit@ccdc.cam.ac.uk.
77. I. Vögtle, E. Weber, Angew. Chem. 1974, 86, 896-898; Angew. Chem. Int. Ed. Engl. 1974, 13, 814-816.
78. I. Vögtle, E. Weber, Angew. Chem. 1974, 86, 896-898; Angew. Chem. Int. Ed. Engl. 1974, 13, 814-816.
79. C. Krüger, M. Yalpani, Chem. Ber. 1983, 776, 3359-3365.
80. Van der Waals radii [Å] C 1.70, H 1.20, O 1.52; compare, A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
81. D. J. Iverson, G. Hunter, J. F. Blount, J. R. Damewood, K. Mislow, J Am. Chem. Soc. 1981, 703, 6073-6083.
82. The X-ray crystal structure analysis of the hexaalkenyltriphenylene 25 does establish its structure, but the unsatisfactorily high R values do not permit to discuss any structural peculiarities of 25 in detail.
83. X. Zhou, M. K. Tse, T. S. M. Wan, K. S. Chan, J. Org. Chem. 1996, 61, 3590-3593.
84. a) J. M. Bollinger, J. J. Burke, E. M. Arnett, J. Org. Chem. 1966, 31, 1310;
85. b) E. M. Arnett, J. M. Bollinger, J. C. Sanda, J. Am. Chem. Soc. 1965, 87, 2050-2051.
86. D. Seyferth, G. Singh, J. Am. Chem. Soc. 1965, 87, 4156-4162.
87. F. D. Lewis, G. D. Reddy, D. M. Bassani, S. Schneider, M. Gahr, J. Am. Chem. Soc. 1994, 116, 597-605.
88. M. A. Ogliaruso, E. I. Becker, J. Org. Chem. 1965, 30, 3354-3360.
89. J. D. Debad, S. K. Lee, X. Qiao, R. A. Pascal, A. J. Bard, Acta Chem. Scand. 1998, 52, 45-50.
90. R. W. Denny, A. Nickon, Org. React. 1973, 20, 133-336.
91. a) S. Mazur, C. S. Foote, J Am. Chem. Soc. 1970, 92, 3225-3226;
92. b) P. D. Bartlett, A. P. Schaap, J. Am. Chem. Soc. 1970, 92, 3223-3225.
93. H. Meier, H. C. Holst, Adv. Synth. Catal. 2003, 345, 1005-1011.
94. L. F. Tietze, T. Eicher, Reaktionen und Synthesen, Thieme, Stuttgart, 1991.
95. A. B. Holmes, C. N. Sporikou, Org. Synth. 1987, 65, 61-67.
96. F. Stein, Dissertation, Universität Göttingen, 1994.
97. M. F. Ansell, M. A. Davis, J. W Hancock, W. J. Hickinbottom, P. G. Holton, A. A. Hyatt, J. Chem. Soc. 1955, 2705-2707.
98. R. F. Cunico, F. J. Clayton, J. Org. Chem. 1976, 41, 1480-1482.
99. R. Breslow, B. Jaun, R. Q. Kluttz, C.-Z. Xia, Tetrahedron 1982, 38, 863-867.
100. Octabromonaphthalene was prepared according to the literature procedure, but diphenyl ether was used instead of toluene to recrystallize the product: J. H. Brady, A. D. Redhouse, B. J. Wakefield, J. Chem. Res. Miniprint 1982, 6, 1541-1554.
101. J. E. Leibner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450.
102. G. M. Sheldrick in Computational crystallography (Ed.: D. Sayre), Oxford University Press, New York, 1982, pp. 506-514.