Preparation of functionalized biaryl compounds via cross-coupling reactions of aryltrialkoxysilanes with aryl bromides

Chemical Communications

Volumn , Issue 14, 1997, Pages 1309-1310

  Shibata, Koichi ^a   Miyazawa, Kazutoshi ^a   Goto, Yasuyuki ^a  

^a CHISSO CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542397449     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701770g     Document Type: Article

References (21)

1. D. Demus, H. Demus and H. Zaschke, Flüssige Kristalle in Tabellen, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1976; D. Demus and H. Zaschke, Flüssige Kristalle in fabellen II, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1994; G. W. Gray and G. R. Luckhurst, The Molecular Physics of Liquid Crystal, Academic Press, New York, London, Toronto, Sydney and San Francisco, 1979.
2. D. Demus, H. Demus and H. Zaschke, Flüssige Kristalle in Tabellen, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1976; D. Demus and H. Zaschke, Flüssige Kristalle in fabellen II, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1994; G. W. Gray and G. R. Luckhurst, The Molecular Physics of Liquid Crystal, Academic Press, New York, London, Toronto, Sydney and San Francisco, 1979.
3. D. Demus, H. Demus and H. Zaschke, Flüssige Kristalle in Tabellen, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1976; D. Demus and H. Zaschke, Flüssige Kristalle in fabellen II, VEB Deutsche Verlag für Grundstoff Industrie, Leipzig, 1994; G. W. Gray and G. R. Luckhurst, The Molecular Physics of Liquid Crystal, Academic Press, New York, London, Toronto, Sydney and San Francisco, 1979.
4. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
5. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
6. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
7. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
8. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
9. For reviews of the preparation of biaryls, see (a) M. T. Sainsbury, Tetrahedron, 1980, 36, 3327; (b) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977;. (c) T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471; (d) D. W. Knight, Comprehensive Organic Synthesis, Pergamon Press, Oxford, New York, Seoul and Tokyo, vol. 3, pp. 499-516, 1991; (e) N. Miyaura and A. Suzuki, Synth. Org. Chem. Jpn., 1988, 46, 848; (f) A. Suzuki and N. Miyaura. J. Synth. Org. Chem. Jpn., 1993, 51, 1043.
10. Y. Hatanaka and T. Hiyama, J. Synth. Org. Chem. Jpn., 1990, 48, 834; Y. Hatanaka, K. Goda, Y. Okahara and T. Hiyama, Tetrahedron, 1994, 50, 8301.
11. Y. Hatanaka and T. Hiyama, J. Synth. Org. Chem. Jpn., 1990, 48, 834; Y. Hatanaka, K. Goda, Y. Okahara and T. Hiyama, Tetrahedron, 1994, 50, 8301.
12. For the reactions of organometallic reagents with tetrachlorosilane, see: L. W. Breed and W. J. Haggerty, J. Org. Chem., 1960, 25, 126; W. Laarz, M. Schulten, R. Boese and D. Blaeser, Z. Naturfursch. B. Chem. Sci., 1992, 47, 1233; N. Auner, R. Probst, F. Hahn and E. Herdtweck, J. Organomet. Chem., 1993, 459, 25.
13. For the reactions of organometallic reagents with tetrachlorosilane, see: L. W. Breed and W. J. Haggerty, J. Org. Chem., 1960, 25, 126; W. Laarz, M. Schulten, R. Boese and D. Blaeser, Z. Naturfursch. B. Chem. Sci., 1992, 47, 1233; N. Auner, R. Probst, F. Hahn and E. Herdtweck, J. Organomet. Chem., 1993, 459, 25.
14. For the reactions of organometallic reagents with tetrachlorosilane, see: L. W. Breed and W. J. Haggerty, J. Org. Chem., 1960, 25, 126; W. Laarz, M. Schulten, R. Boese and D. Blaeser, Z. Naturfursch. B. Chem. Sci., 1992, 47, 1233; N. Auner, R. Probst, F. Hahn and E. Herdtweck, J. Organomet. Chem., 1993, 459, 25.
15. For the reactions of organometallic reagents with tetramethoxysilane, see: T. G. Selin and R. West, J. Am. Chem. Soc., 1962, 84, 1856; R. Tacke, A. Mentlage-Falten, H. Linoh and S. Magada, Z. Naturforsch., B; Anorg Chem., Org. Chem., 1986, 41B, 649; A. Hosomi, S. Kohra, K. Ogata, T. Yanagi and Y. Tominaga, J. Org. Chem., 1990, 55, 2415.
16. For the reactions of organometallic reagents with tetramethoxysilane, see: T. G. Selin and R. West, J. Am. Chem. Soc., 1962, 84, 1856; R. Tacke, A. Mentlage-Falten, H. Linoh and S. Magada, Z. Naturforsch., B; Anorg Chem., Org. Chem., 1986, 41B, 649; A. Hosomi, S. Kohra, K. Ogata, T. Yanagi and Y. Tominaga, J. Org. Chem., 1990, 55, 2415.
17. For the reactions of organometallic reagents with tetramethoxysilane, see: T. G. Selin and R. West, J. Am. Chem. Soc., 1962, 84, 1856; R. Tacke, A. Mentlage-Falten, H. Linoh and S. Magada, Z. Naturforsch., B; Anorg Chem., Org. Chem., 1986, 41B, 649; A. Hosomi, S. Kohra, K. Ogata, T. Yanagi and Y. Tominaga, J. Org. Chem., 1990, 55, 2415.
18. Y. Goto, T. Ogawa, S. Sawada and S. Sugimon, Mol. Cryst. Liq. Cryst., 1991, 209, 1.
19. H. J. Plach, B. Rieger, E. Poetsch and V. Reiffenrath, Proc. 10th Int. Disp. Res. Conf. 1990, 136; G. Weber, U. Finkenzelle, T. Geelhaar, H. J. Plach, B. Rieger and L. Pohl, Liq. Cryst., 1989, 5, 1381; H. J. Plach, G. Weber and B. Rieger, Proc. SID Int. Symp., 1990, 91.
20. H. J. Plach, B. Rieger, E. Poetsch and V. Reiffenrath, Proc. 10th Int. Disp. Res. Conf. 1990, 136; G. Weber, U. Finkenzelle, T. Geelhaar, H. J. Plach, B. Rieger and L. Pohl, Liq. Cryst., 1989, 5, 1381; H. J. Plach, G. Weber and B. Rieger, Proc. SID Int. Symp., 1990, 91.
21. H. J. Plach, B. Rieger, E. Poetsch and V. Reiffenrath, Proc. 10th Int. Disp. Res. Conf. 1990, 136; G. Weber, U. Finkenzelle, T. Geelhaar, H. J. Plach, B. Rieger and L. Pohl, Liq. Cryst., 1989, 5, 1381; H. J. Plach, G. Weber and B. Rieger, Proc. SID Int. Symp., 1990, 91.