Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki-Heck reaction

Applied Catalysis A: General

Volumn 362, Issue 1-2, 2009, Pages 163-168

  Nadri, Shirin ^a   Joshaghani, Mohammad ^a,b   Rafiee, Ezzat ^a,b  

^a RAZI UNIVERSITY   (Iran)

^b Kermanshah Oil Refining Company   (Iran)

Author keywords

Biphenyl based phosphine; C C coupling; Mizoroki Heck Reaction; Palladium catalyst

Indexed keywords

AIR-STABLE; ARYL HALIDES; BENEFICIAL EFFECTS; BIPHENYL-BASED PHOSPHINE; C-C COUPLING; CATALYTIC SYSTEM; CROSS-COUPLING; ELECTRON-RICH; HECK REACTIONS; MIZOROKI-HECK REACTION; PALLADIUM CATALYST; RATE DETERMINING STEP; REACTION TIME; STEREO-SELECTIVE;

CATALYSIS; CATALYSTS; OLEFINS; PALLADIUM; PHOSPHORUS COMPOUNDS;

COORDINATION REACTIONS;

EID: 66149106319     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2009.04.038     Document Type: Article

References (51)

1. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581
2. Heck R.F., and Nolley J.P. J. Org. Chem. 37 (1972) 2320-2322
3. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009-3066
4. Sakoda K., Mihara J., and Ichikawa J. Chem. Commun. (2005) 4684-4686
5. Arnold L.A., Luo W., and Guy R.K. Org. Lett. 6 (2004) 3005-3007
6. Dounay A.B., Overman L.E., and Wrobleski A.D. J. Am. Chem. Soc. 127 (2005) 10186-10187
7. Mo J., Xu L., Ruan J., Liu S., and Xiao J. Chem. Commun. (2006) 3591-3593
8. Tu T., Hou X.-L., and Dai L.-X. Org. Lett. 5 (2003) 3651-3653
9. Mariampillai B., Herse C., and Lautens M. Org. Lett. 7 (2005) 4745-4747
10. de Meijere A., and Meyer F.E. Angew. Chem. Int. Ed. 33 (2004) 2379-2411
11. Morales-Morales D., Redón R., Yung C., and Jensen C.M. Chem. Commun. (2000) 1619-1620
12. Littke A.F., and Fu G.C. J. Org. Chem. 64 (1999) 10-11
13. Shaughnessy K.H., Kim P., and Hartwig J.F. J. Am. Chem. Soc. 121 (1999) 2123-2132
14. Ehrentraut A., Zapf A., and Beller M. Synlett (2000) 1589-1592
15. Portnoy M., Ben-David Y., Rousso I., and Milstein D. Organometallics 13 (1994) 3465-3479
16. Whitcombe N.J., Hii K.K., and Gibson S.E. Tetrahedron 57 (2001) 7449-7476
17. Bedford R.B. Chem. Commun. (2003) 1787-1796
18. Old D.W., Wolfe J.P., and Buchwald S.L. J. Am. Chem. Soc. 120 (1998) 9722-9723
19. Wolfe J.P., and Buchwald S.L. Angew. Chem. Ind. Ed. 38 (1999) 2413-2416
20. Wolfe J.P., Tomori H., Sadighi J.P., Yin J.J., and Buchwald S.L. J. Org. Chem. 65 (2002) 1158-1174
21. Vorogushin A.V., Huang X.H., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 8146-8149
22. Burgos C.H., Barder T.E., Huang X.H., and Buchwald S.L. Angew. Chem. Ind. Ed. 45 (2006) 4321-4326
23. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685-4696
24. Billingsley K.L., Anderson K.W., and Buchwald S.L. Angew. Chem. Ind. Ed. 45 (2006) 3484-3488
25. Milne J.E., and Buchwald S.L. J. Am. Chem. Soc. 126 (2004) 13028-13032
26. Fox J.M., Huang X.H., Chieffi A., and Buchwald S.L. J. Am. Chem. Soc. 122 (2000) 1360-1370
27. Moradi W.A., and Buchwald S.L. J. Am. Chem. Soc. 123 (2002) 7996-8002
28. Strieter E.R., Blackmond D.G., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 13978-13980
29. Joshaghani M., Daryanavard M., Rafiee E., Xiao J., and Baillie C. Tetrahedron Lett. 48 (2007) 2025-2027
30. Joshaghani M., Faramarzi E., Rafiee E., Daryanavard M., Xiao J., and Baillie C. J. Mol. Catal. A: Chem. 273 (2007) 310-315
31. Trzeciak A.M., and Ziółkowski J. J. Coord. Chem. Rev. 249 (2005) 2308-2322
32. Frey G.D., Schütz J., Herdtweck E., and Herrmann W.A. Organometallics 24 (2005) 4416-4426
33. Reetz M.T., and de Vries J.G. Chem. Commun. (2004) 1559-1563
34. de Vries J.G. Dalton Trans. (2006) 421-429
35. Gruber A.S., Pozebon D., Monteiro A.L., and Dupont J. Tetrahedron Lett. 42 (2001) 7345-7348
36. de Vries A.H.M., Mulders J.M.C.A., Mommers J.H.M., Henderickx H.J.W., and de Vries J.G. Org. Lett. 5 (2003) 3285-3288
37. Herrmann W.A., Brössmer C., Öfele K., Beller M., and Fischer H. J. Mol. Catal. 103 (1995) 133-146
38. Zhao F., Bhanage B.M., Shirai M., and Arai M. J. Mol. Catal. A: Chem. 142 (1999) 383-388
39. Beller M., and Riermeier T.H. Eur. J. Inorg. Chem. (1998) 29-35
40. Hahn F.E., Jahnke M.C., Gomez-Benitez V., Morales-Morales D., and Pape T. Organometallics 24 (2005) 6458-6463
41. Amatore C., and Jutand A. Acc. Chem. Res. 33 (2000) 314-321
42. Stambuli J.P., Stauffer S.R., Shaughnessy K.H., and Hartwig J.F. J. Am. Chem. Soc. 123 (2001) 2677-2678
43. Zapf A., and Beller M. Chem. Eur. J. 7 (2001) 2908-2915
44. Böhm V.P.W., and Herrmann W.A. Chem. Eur. J. 7 (2001) 4191-4197
45. Littke A.F., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 6989-7000
46. Herrmann W.A., Brössmer C., Reisinger C.-P., Riermeier T.H., Öfele k., and Beller M. Chem. Eur. J. 3 (1997) 1346-1357
47. van Strijdonck G.P.F., Boele M.D.K., Kamer P.C.J., de Vries J.G., and van Leeuwen P.W.N.M. Eur. J. Inorg. Chem. (1999) 1073-1076
48. Liu S., Berry N., Thomson N., Pettman A., Hyder Z., Mo J., and Xiao J. J. Org. Chem. 71 (2006) 7467-7470
49. Consorti C.S., Flores F.R., and Dupont J. J. Am. Chem. Soc. 127 (2005) 12054-12065
50. Schmidt A.F., and Smirnov V.V. Kin. Catal. 44 (2003) 518-523
51. Schmidt A.F., Al-Halaiqa A., and Smirnov V.V. Kin. Catal. 48 (2007) 716-727