Collect. Czech. Chem. Commun. 2004, 69, 1517-1536
https://doi.org/10.1135/cccc20041517

Novel Route to Enantiopure 2,2'-Diaryl-1,1'-binaphthalenes by Stereoconservative Suzuki Arylation at Positions 2 and 2'

Henrich Brath, Margaréta Dubovská, Michal Juríček, Peter Kasák and Martin Putala*

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovak Republic

References

1. Preliminary communication: Kasák P., Brath H., Dubovská M., Juríček M., Putala M.: Tetrahedron Lett. 2004, 45, 791. <https://doi.org/10.1016/j.tetlet.2003.11.017>
2. Putala M.: Enantiomer 1999, 4, 243; and references therein.
3. Pu L.: Chem. Rev. 1998, 98, 2405; and references therein. <https://doi.org/10.1021/cr970463w>
4. Tefler S. G., Kuroda R.: Coord. Chem. Rev. 2003, 243, 33; and references therein.
5. For example see: Nelson T. D., Meyers A. I.: J. Org. Chem. 1994, 59, 2655. <https://doi.org/10.1021/jo00088a066>
6. Charmant J. P. H., Falis I. A., Hunt N. J., Lloyd-Jones G. C., Murray M., Nowak T.: J. Chem. Soc., Dalton Trans. 2000, 1723. <https://doi.org/10.1039/b000651n>
7. For example see: Uozomi Y., Kyota H., Kishi E., Hayashi T.: Tetrahedron: Asymmetry 1996, 7, 1603. <https://doi.org/10.1016/0957-4166(96)00193-0>
8. Halterman R. L., Ramsey T. M.: J. Organomet. Chem. 1997, 530, 225. <https://doi.org/10.1016/S0022-328X(96)06635-1>
9. Nishida J., Suzuki T., Ohkita M., Tsuji T.: Angew. Chem., Int. Ed. 2001, 40, 3251. <https://doi.org/10.1002/1521-3773(20010903)40:17<3251::AID-ANIE3251>3.0.CO;2-P>
10. Kasák P., Mikláš R., Putala M.: J. Organomet. Chem. 2001, 637–639, 318. <https://doi.org/10.1016/S0022-328X(01)00926-3>
11. Schilling B., Kaufmann D. E.: Eur. J. Org. Chem. 1998, 701. <https://doi.org/10.1002/(SICI)1099-0690(199804)1998:4<701::AID-EJOC701>3.0.CO;2-E>
12. For example, Suzuki coupling of 3,3′-diiodo derivative: Simonson D. L., Kingsbury K., Xu M. H., Hu Q. S., Sabat M., Pu L.: Tetrahedron 2002, 58, 8189. <https://doi.org/10.1016/S0040-4020(02)00967-5>
13. For example, Suzuki coupling of 6,6′-dibromo derivative: Jiang J., Liu H. W., Zhao Y. L., Chen C. F., Xi F.: J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 1167. <https://doi.org/10.1002/pola.10205>
14. Chaumeil H., Signorella S., Le Driean C.: Tetrahedron 2000, 56, 9655; and references therein. <https://doi.org/10.1016/S0040-4020(00)00928-5>
15. Kotha S., Lahiri K., Kashinath D.: Tetrahedron 2002, 58, 9633; and references therein. <https://doi.org/10.1016/S0040-4020(02)01188-2>
16. Putala M.: Chem. Listy 2001, 95, 353.
17. Schilling B., Kaiser V., Kaufmann D. E.: Chem. Ber. 1997, 130, 923. <https://doi.org/10.1002/cber.19971300718>
18. Brown K. J., Berry M. S., Waterman K. C., Lingenfelter D., Murdoch J. R.: J. Am. Chem. Soc. 1984, 106, 4717. <https://doi.org/10.1021/ja00329a014>
19. Hoshi T., Shionoiri H., Suzuki T., Ando M., Hagiwara H.: Chem. Lett. 1999, 1245. <https://doi.org/10.1246/cl.1999.1245>
20. Oh T., Lopez P., Reilly M.: Eur. J. Org. Chem. 2000, 2901. <https://doi.org/10.1002/1099-0690(200008)2000:16<2901::AID-EJOC2901>3.0.CO;2-0>
21. Hoshi T., Shionoiri H., Katano M., Suzuki T., Hagiwara H.: Tetrahedron: Asymmetry 2002, 13, 2167. <https://doi.org/10.1016/S0957-4166(02)00578-5>
22. Miyashita A., Takaya H., Souchi T., Noyori R.: Tetrahedron 1984, 40, 1245. <https://doi.org/10.1016/S0040-4020(01)82411-X>
23. For example see: Murata M., Oyama T., Watanabe S., Masuda Y.: J. Org. Chem. 2000, 65, 164. <https://doi.org/10.1021/jo991337q>
24. For example see: Chaumeil H., Signorella S., Le Drain C.: Tetrahedron 2000, 56, 9655. <https://doi.org/10.1016/S0040-4020(00)00928-5>
25. Littke A. F., Dai C., Fu G. C.: J. Am. Chem. Soc. 2000, 122, 4020. <https://doi.org/10.1021/ja0002058>
26. Brown K. J., Berry M. S., Murdoch J. R.: J. Org. Chem. 1985, 50, 4345. <https://doi.org/10.1021/jo00222a029>
27. Vonenhof M., Patay J.: Tetrahedron Lett. 1990, 31, 985. <https://doi.org/10.1016/S0040-4039(00)94409-5>
28. Mash E. A., Hemperly S. B., Nelson K. A., Heidt P. C., van Deusen S.: J. Org. Chem. 1990, 55, 2045. <https://doi.org/10.1021/jo00294a016>
29. Li J., Rajca A., Rajca S.: Synth. Met. 2003, 137, 1507. <https://doi.org/10.1016/S0379-6779(02)01205-5>