Biaryl synthesis using highly stable aryl[2-(hydroxymethyl)phenyl]dimethylsilanes and aryl iodides under fluoride-free conditions

Science and Technology of Advanced Materials

Volumn 7, Issue 6, 2006, Pages 536-543

  Nakao, Yoshiaki ^a   Sahoo, Akhila K ^a   Yada, Akira ^a   Chen, Jinshui ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Biaryl; Cross coupling reaction; Palladium; Silicon

Indexed keywords

ARYL IODIDES; COUPLING REACTION; INTRAMOLECULAR COORDINATION;

CATALYSIS; COPPER; MOLECULAR DYNAMICS; REACTION KINETICS; SILICATES;

IODINE COMPOUNDS;

EID: 33749651001     PISSN: 14686996     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.stam.2006.02.019     Document Type: Article

References (31)

1. Stanforth S.P. Tetrahedron 54 (1998) 263
2. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
3. N. Miyaura (Ed.), Cross-Coupling Reactions a Practical Guide, Topics in Current Chemistry, vol. 219, Springer, Berlin, 2002.
4. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley, Weinheim
5. Tsuji J. Palladium Reagents and Catalysts (2004), Wiley, Chichester p. 288
6. T. Hiyama, E. Shirakawa, Organosilicon compounds, in: N. Miyaura (Ed.), Cross-Coupling Reactions a Practical Guide, Topics in Current Chemistry, vol. 219, Springer, Berlin, 2002, p. 61.
7. Denmark S.E., and Sweis R.F. Organosilicon compounds in cross-coupling reactions. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley, Weinheim p. 163
8. Tsuji J. Palladium Reagents and Catalysts (2004), Wiley, Chichester p. 338
9. Hirabayashi K., Mori A., Kawashima J., Suguro M., Nishihara Y., and Hiyama T. J. Org. Chem. 65 (2000) 5342
10. Denmark S.E., and Ober M.H. Adv. Synth. Catal. 346 (2004) 1703
11. Sahoo A.K., Oda T., Nakao Y., and Hiyama T. Adv. Synth. Catal. 346 (2004) 1715
12. Hagiwara E., Gouda K.i., Hatanaka Y., and Hiyama T. Tetrahedron Lett. 38 (1997) 439
13. Wolf C., and Lerebours R. Org. Lett. 6 (2004) 1147
14. Ito H., Sensui H., Arimoto K., Miura K., and Hosomi A. Chem. Lett. (1997) 639
15. Pierrat P., Gros P., and Fort Y. Org. Lett. 7 (2005) 697
16. Taguchi H., Takami K., Tsubouchi A., and Takeda T. Tetrahedron Lett. 45 (2004) 429
17. For a preliminary communication, see. Nakao Y., Imanaka H., Sahoo A.K., Yada A., and Hiyama T. J. Am. Chem. Soc. 127 (2005) 6952
18. Hudrlik P.F., Abdallah Y.M., and Hudrlik A.M. Tetrahedron Lett. 33 (1992) 6747
19. Hudrlik P.F., Arango J.O., Hijji Y.M., Okoro C.O., and Hudrlik A.M. Can. J. Chem. 78 (2000) 1421
20. Yoshida H., Shirakawa E., Kurahashi T., Nakao Y., and Hiyama T. Organometallics 19 (2000) 5671
21. Frisell C., and Lawesson S.-O. Org. Synth. Coll. 5 (1972) 642
22. Mowery M.E., and DeShong P. J. Org. Chem. 64 (1999) 3266
23. Rao M.S.C., and Rao G.S.K. Synthesis (1987) 231
24. Michael S.W., and DeShong P. J. Org. Chem. 69 (2004) 1137
25. Clive D.L.J., and Kang S. J. Org. Chem. 66 (2001) 6083
26. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550
27. Sato N. J. Org. Chem. 17 (1978) 3367
28. Xiong Z., Wang N., Dai M., Li A., Chen J., and Yang Z. Org. Lett. 6 (2004) 3337
29. Iminophosphine ligands were reported effective also for the cross-coupling reaction of organostannanes with aryl halides (the Kosugi-Migita-Stille reaction), see. Shirakawa E., Yoshida H., and Takaya H. Tetrahedron Lett. 38 (1997) 3759
30. Chult C., Corriu R.J.P., Reye C., and Young J.C. Chem. Rev. 93 (1993) 1371
31. Holmes R.R. Chem. Rev. 96 (1996) 927