Application of the Suzuki reaction as the key step in the synthesis of a novel atropisomeric biphenyl derivative for use as a liquid crystal dopant

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6832-6835

  Cammidge, Andrew N ^a   Crépy, Karen V L ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DEBORONATION;

CHEMICAL REACTIONS; DERIVATIVES; HYDROLYSIS; LIQUID CRYSTALS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

BIPHENYL DERIVATIVE; BORONIC ACID DERIVATIVE;

ARTICLE; DIPOLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIQUID CRYSTAL; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0042890576     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034652s     Document Type: Article

References (36)

1. Dewick, P. M. Medicinal Natural Products; Wiley: Chichester, UK, 2002.
2. Pu, L. Chem. Rev. 1998, 98, 2405.
3. Collings, P. J.; Hird, M. Introduction to Liquid Crystals-Chemistry and Physics; Taylor and Francis: London, UK, 1997.
4. Goodby, J. W.; Clark, N. A.; Laggerwall, S. T. Ferroelectric Liquid Crystals: Principles, Properties and Applications; Gordon and Breach: Philadelphia, PA, 1991.
5. (a) Gray, G. W.; Hird, M.; Lacey, D.; Toyne, K. J. Mol. Cryst. Liq. Cryst. 1990, 191, 1.
6. (b) Gray, G. W.; Hird, M.; Lacey, D.; Toyne, K. J. J. Chem. Soc., Perkin Trans. 2 1989, 2041.
7. (c) Glendenning, M. E.; Goodby, J. W.; Hird, M.; Lacey, D.; Toyne, K. J. J. Chem. Soc., Perkin Trans. 2 2000, 27.
8. (d) Glendenning, M. E.; Goodby, J. W.; Hird, M.; Lacey, D.; Toyne, K. J. J. Chem. Soc., Perkin Trans. 2 1999, 481.
9. Lemieux, R. P. Acc. Chem. Res. 2001, 34, 845.
10. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
11. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
12. Buchwald has recently reported an improved catalyst for coupling certain sterically hindered substrates: Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
13. Fu has recently reported that Negishi coupling can be successfully employed to couple hindered substrates but noted that homocoupling was a significant side reaction when tetra-o-substituted biphenyls were synthesized: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
14. Cammidge, A. N.; Crépy, K. V. L. Chem. Commun. 2000, 1723.
15. A diastereoselective Suzuki coupling was reported by Nicolaou: Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T.-Y.; Natarajan, S.; Chu, X.-J.; Bräse, S.; Rübsam, F. Chem. Eur. J. 1999, 5, 2584.
16. (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051.
17. (b) Castanet, A.-S.; Colbert, F.; Broutin, P.-E.; Obringer, M. Tetrahedron: Asymmetry, 2002, 13, 659.
18. (a) Stanley, W. M.; Adams, R. J. Am. Chem. Soc. 1930, 52, 1200.
19. (b) Kleiderer, E. C.; Adams, R. J. Am. Chem. Soc. 1933, 55, 4219.
20. (c) Kawano, N.; Okigawa, M.; Hasaka, N.; Kouno, I.; Kawahara, Y.; Fujita, Y. J. Org. Chem., 1981, 46, 389.
21. McKillop, A.; Howarth, B. D.; Kobylecki, R. J. Synth. Commun. 1974, 19, 865.
22. Slocum, D. W.; Dietzel, P. Tetrahedron Lett. 1999, 40, 1823.
23. (a) Ritter, K. Synthesis 1993, 735.
24. (b) Cabri, W.; De Bernardinis, S.; Francalanci, F.; Penco, S. J. Org. Chem. 1990, 55, 350.
25. (c) Cacchi, S.; Ciattini, P. G.; Morera, E.; Orta, G. Tetrahedron Lett. 1986, 27, 5541.
26. Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 5458.
27. Fuson, R. C.; Corse, J.; Welldon, P. B. J. Am. Chem. Soc. 1941, 63, 2645.
28. Kobayashi, Y.; Shiozaki, M.; Ando, O. J. Org. Chem. 1995, 60, 2570.
29. Yamazaki, S.; Yamazaki, Y. Bull. Chem. Soc. Jpn. 1990, 63, 301.
30. Yamazaki, S. Synth. Commun. 1997, 27, 3559.
31. (a) Capdevielle, P.; Lavigne, A.; Maumy, M. Synthesis 1989, 453.
32. (b) Capdevielle, P.; Lavigne, A.; Sparfel, D.; Baranne-Lafont, J.; Cuong, N. K.; Maumy, M. Tetrahedron Lett. 1990, 31, 3305.
33. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett. 1992, 207.
34. Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933.
35. Widdowson, D. A.; Zhang, Y.-Z. Tetrahedron 1986, 42, 2111.
36. It is interesting to compare our results to those of Buchwald [ref 8], who reported that strictly anhydrous conditions were required to prevent destruction of the bromide coupling partner, an observation that further emphasizes the mechanistic balance required for successful coupling of hindered substrates.