Lewis acid-assisted oxidative cross-coupling of 2-naphthol derivatives with copper catalysts

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4325-4331

  Yan, Pei ^a   Sugiyama, Yukihiro ^a   Takahashi, Yusuke ^a   Kinemuchi, Haruki ^a   Temma, Tomohisa ^a   Habaue, Shigeki ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

Binaphthol; Cross coupling; Lewis acid; Oxidative coupling

Indexed keywords

2 NAPHTHOL; 2,2' DIHYDROXY 1,1' BINAPHTHYL; COPPER; LEWIS ACID; OXYGEN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 41549086457     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.080     Document Type: Article

References (31)

1. Preliminary communication:. Habaue S., Temma T., Sugiyama Y., and Yan P. Tetrahedron Lett. 48 (2007) 8595-8598
2. Brunel J.M. Chem. Rev. 105 (2005) 857-897
3. Reactions with an excess amount of copper complex:
4. Hovorka M., Ščigel R., Gunrerová J., Tichý M., and Závada J. Tetrahedron 48 (1992) 9503-9516
5. Hovorka M., and Závada J. Tetrahedron 48 (1992) 9517-9530
6. Smrčina M., Vyskočil S., Máca B., Polákova J., Claxton T.A., Abbot A.P., and Kočovský P. J. Org. Chem. 59 (1994) 2156-2163
7. Reports including results on a catalytic reaction:
8. Smrčina M., Polákova J., Vyskočil S., and Kočovský P. J. Org. Chem. 58 (1993) 4534-4538
9. Hon S.-W., Li C.-H., Kuo J.-H., Barhate N.B., Liu Y.-H., Wang Y., and Chen C.-T. Org. Lett. 3 (2001) 869-872
10. Caselli A., Giovenzana G.B., Palmisamo G., Sisti M., and Pilati T. Tetrahedron: Asymmetry 14 (2003) 1451-1454
11. Habaue S., Seko T., and Okamoto Y. Macromolecules 36 (2003) 2604-2608
12. Habaue S., Seko T., Isonaga M., Ajiro H., and Okamoto Y. Polym. J. 35 (2003) 592-597
13. Temma T., and Habaue S. Tetrahedron Lett. 46 (2005) 5655-5657
14. Temma T., Hatano B., and Habaue S. Tetrahedron 62 (2006) 8559-8563
15. Habaue S., Takahashi Y., and Temma T. Tetrahedron Lett. 48 (2007) 7301-7304
16. Yamamoto Y., Onuki S., Yumoto M., and Asano N. J. Am. Chem. Soc. 116 (1994) 421-422
17. Sibi M.P., and Porter N.A. Acc. Chem. Res. 32 (1999) 163-171
18. Srikanth G.S.C., and Castle S.L. Tetrahedron 61 (2005) 10377-10441
19. Zimmerman J., and Sibi M.P. Top. Curr. Chem. 263 (2006) 107-162
20. Homo-coupling reaction in the presence of chlorotrimethylsilane was reported:. Chu C.-Y., Hwang D.-R., Wang S.-K., and Uang B.-J. Chem. Commun. (2001) 980-981
21. Temma T., Hatano B., and Habaue S. Polymer 47 (2006) 1845-1851
22. Noji M., Nakajima M., and Koga K. Tetrahedron Lett. 35 (1994) 7983-7984
23. Nakajima M., Hashimoto S., Noji M., and Koga K. Chem. Pharm. Bull. 46 (1998) 1814-1815
24. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S., Noji M., and Koga K. J. Org. Chem. 64 (1999) 2264-2271
25. Smrčina M., Lorenc M., Hanuš V., Sedmera P., and Kočovský P. J. Org. Chem. 57 (1992) 1917-1920
26. Zhang Y., Yeung S.-M., Wu H., Heller D.P., Wu C., and Wulff W.D. Org. Lett. 5 (2003) 1813-1816
27. Dennis M.R., and Woodward S. J. Chem. Soc., Perkin Trans. 1 (1998) 1081-1085
28. Temma T., and Habaue S. J. Polym. Sci., Part A: Polym. Chem. 43 (2005) 6287-6294
29. Temma T., Takahashi Y., Yoshii Y., and Habaue S. Polym. J. 39 (2007) 524-530
30. Habaue S., Temma T., Takahashi Y., and Yan P. Kobunshi Ronbunshu 64 (2007) 617-626
31. Temma T., and Habaue S. J. Polym. Sci., Part A: Polym. Chem. 46 (2008) 1034-1041