Ferrocenyl phosphine-oxazaphospholidine oxide ligands for the Suzuki-Miyaura coupling of hindered aryl bromides and chlorides

Canadian Journal of Chemistry

Volumn 87, Issue 1 SPEC. ISS., 2009, Pages 171-175

  Vinci, Daniele ^a   Martins, Nelson ^b   Saidi, Ourida ^a   Bacsa, John ^a   Brigas, Amadeu ^b   Xiao, Jianliang ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b UNIVERSIDADE DO ALGARVE   (Portugal)

Author keywords

Aryl bromides; Aryl chlorides; Ferrocenyl phosphines; Palladium; Suzuki Miyaura coupling

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYL CHLORIDES; AS-LIGANDS; ASYMMETRIC INDUCTION; BORONIC ACID; COUPLING REACTION; FERROCENYL; FERROCENYL PHOSPHINES; SUZUKI-MIYAURA COUPLING; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

ACIDS; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; PALLADIUM; PHOSPHORUS COMPOUNDS; SEMICONDUCTING INDIUM GALLIUM ARSENIDE;

LIGANDS;

EID: 67650908459     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V08-113     Document Type: Article

References (45)

1. A. Suzuki. Acc. Chem. Res. 15, 178 (1982).
2. A. Suzuki. Pure Appl. Chem. 57, 1749 (1985).
3. N. Miyaura and A. Suzuki. J. Synth. Org. Chem. Jpn. 46, 848 (1988).
4. A. Suzuki. Pure Appl. Chem. 63, 419 (1991).
5. N. Miyaura and A. Suzuki. J. Synth. Org. Chem. Jpn. 51, 1043 (1993).
6. A. Suzuki. Pure Appl. Chem. 66, 213 (1994).
7. N. Miyaura and A. Suzuki. Chem. Rev. 95, 2457 (1995).
8. S. Liu and J. Xiao. J. Mol. Catal. A: Chem. 270, 1 (2007).
9. G. Bringmann, R. Walter, and R. Weirich. Angew. Chem. Int. Ed. 29, 977 (1990).
10. T.G. Gant and A.I. Meyers. Tetrahedron, 50, 2297 (1994).
11. A.I. Meyers, J.R. Flisak, and R.A. Aitken. J. Am. Chem. Soc. 109, 5446 (1987).
12. K. Kamikawa and M. Uemera. Synlett, 938 (2000).
13. M. Uemura, A. Daimon, and Y. Hayashi. J. Chem. Soc. Chem. Commun. 1943 (1995).
14. K. Kamikawa, A. Tachibana, S. Sugimoto, and M. Uemura. Org. Lett. 3, 2033 (2001).
15. G. Bringmann, M. Breuning, and S. Tasler. Synthesis, 4, 525 (1999).
16. G. Bringmann and D. Menche. Acc. Chem. Res. 34, 615 (2001).
17. K.C. Nicolaou, H. Li, C.N.C. Boddy, J.M. Ramanjulu, T.Y. Yue, S. Natarajan, X.J. Chu, S. Brase, and F. Rubsam. Chem. Eur. J. 5, 2584 (1999).
18. J. Yin and S.L. Buchwald. J. Am. Chem. Soc. 122, 12051 (2000).
19. M. Genov, A. Almorin, and P. Espinet. Chem. Eur. J. 12, 9346 (2006).
20. S.D. Walker, T.E. Barder, J.R. Martinelli, and S.L. Buchwald. Angew. Chem. Int. Ed. 43, 1871 (2004).
21. J. Yin, M.P. Rainka, X.X. Zhang, and S.L. Buchwald. J. Am. Chem. Soc. 124, 1162 (2002).
22. J.P. Wolfe and S.L. Buchwald. Angew. Chem. Int. Ed. 38, 2413 (1999).
23. J.P. Wolfe, R.A. Sinjer, B.H. Yang, and S.L. Buchwald. J. Am. Chem. Soc. 121, 9550 (1999).
24. D.W. Old, J.P. Wolfe, and S.L. Buchwald. J. Am. Chem. Soc. 120, 9722 (1998).
25. N. Gurbuz, I. Ozdemir, S. Demir, and B. Centinkaya. J. Mol. Catal. 209, 23 (2004).
26. S.D. Cho, H.K. Kim, H.S. Yim, M.R. Kim, J.K. Lee, J.J. Kim, and Y.J. Yoond. Tetrahedron, 63, 1345 (2007).
27. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald. J. Am. Chem. Soc. 127, 4685 (2005).
28. N. Marion, O. Navarro, J. Mei, E.D. Steven, N.M. Scott, and S.P. Nolan. J. Am. Chem. Soc. 128, 4101 (2006).
29. K. Billingsley and S.L. Buchwald. J. Am. Chem. Soc. 129, 3358 (2007).
30. A.N. Cammidge and K.V.L. Crépy. Chem. Commun. 1723, (2000).
31. A.N. Cammidge and K.V.L. Crépy. Tetrahedron, 60, 4377 (2004).
32. A.M. Herrbach, O. Baudoin, D. Guénard and F. Guéritte. J. Org. Chem. 68, 4897 (2003).
33. A.S. Castanet, F. Colobert, P.E Broutin, and M. Obringer. Tetrahedron: Asymmetry, 13, 659 (2002).
34. N. Hadei, E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ. Org. Lett. 7, 1991 (2005).
35. R.G. Arrayas, J. Adrio, and J.C. Carretero. Angew. Chem. Int. Ed. 45, 7674 (2006).
36. F.Y. Kwong, W.H. Lam, C.H. Yeung, K.S. Chan, and A.S.C. Chan. Chem. Commun. 1922 (2004).
37. T.E. Pickett, F.X. Roca, and C.J. Richards. J. Org. Chem. 68, 2592 (2003).
38. D. Vinci, N. Mateus, X. Wu, F. Hancock, A. Steiner, and J. Xiao. Org. Lett. 2, 215 (2006).
39. Bruker AXS, Inc. SAINT-PLUS. Version 6.45a [computer program]. Bruker AXS Inc., Madison, Wisconsin. 2005.
40. Bruker AXS, Inc. SADABS. Version 2007-2 [computer program]. Bruker AXS Inc., Madison, Wisconsin. 2007.
41. G.M. Sheldrick. SHELXL-97 [computer program]. University of Göttingen, Germany. 1997.
42. L.J. Barbour. J. Supramol. Chem. 1, 189 (2001).
43. I.D. Hills, M.R. Netherton, and G.C. Fu. Angew. Chem. Int. Ed. 42, 5749 (2003).
44. J.F. Jensen and M. Johannsen. Org. Lett. 5, 3025 (2003).
45. C. Baillie, L. Zhang, and J. Xiao. J. Org. Chem. 69, 7779 (2004).