Ferrocenylmethylphosphines as ligands for room temperature Ni(0)-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl arenesulfonates and aryl chlorides

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2427-2430

  Tang, Zhen Yu ^a   Spinella, Stephen ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; NICKEL; PHOSPHINE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SUZUKI REACTION; TEMPERATURE DEPENDENCE;

EID: 33644845071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.145     Document Type: Article

References (41)

1. D. Zim, V.R. Lando, J. Dupont, and A.L. Monteiro Org. Lett. 3 2001 3049 3051
2. G. Lin, and A. Zhang Tetrahedron 56 2000 7163 7171
3. V. Percec, J.-Y. Bae, M. Zhao, and D.H. Hill J. Org. Chem. 60 1995 176 185
4. For recent reviews: N. Miyaura Topics Curr. Chem. 219 2002 11 59
5. A. Suzuki J. Organomet. Chem. 576 1999 147 168
6. For a recent review: A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176 4211
7. Recent examples of Suzuki cross-coupling reactions involving aryl chlorides as substrates: T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685 4696
8. R. Singh, M.S. Viciu, N. Kramareva, O. Navarro, and S.P. Nolan Org. Lett 7 2005 1829 1832
9. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius J. Am. Chem. Soc. 126 2004 15195 15201
10. J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem., Int. Ed. 41 2003 4746 4748
11. Q.-S. Hu, Y. Lu, Z.-Y. Tang, and H.-B. Yu J. Am. Chem. Soc. 125 2003 2856 2857
12. J.F. Jensen, and M. Johannsen Org. Lett. 5 2003 3025 3028
13. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius Angew. Chem., Int. Ed. 42 2003 3690 3693
14. O. Navarro, R.A. Kelly III, and S.P. Nolan J. Am. Chem. Soc. 125 2003 16194 16195
15. T.E. Pickett, F.X. Roca, and C.J. Richards J. Org. Chem. 68 2003 2592 2599
16. G.A. Grasa, M.S. Viciu, J. Huang, C. Zhang, M.L. Trudell, and S.P. Nolan Organometallics 21 2002 2866 2873
17. N. Kataoka, Q. Shelby, J.P. Stambuli, and J.F. Hartwig J. Org. Chem. 67 2002 5553 5566
18. C.W.K. Gstottmayr, V.P.W. Bohm, E. Herdtweck, M. Grosche, and W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1363 1365
19. S.R. Stauffer, S. Lee, J.P. Stambuli, S.I. Hauck, and J.F. Hartwig Org. Lett. 2 2000 1423 1426
20. Room temperature cross-coupling of one example of electron-deficient aryl tosylate with lithium arylborates was reported: Y. Kobayashi, and R. Mizojiri Tetrahedron Lett. 37 1996 8531 8534
21. M.K. Lakshman, P.F. Thomson, M.A. Nuqui, J.H. Hilmer, N. Sevova, and B. Boggess Org. Lett. 4 2002 1479 1482
22. H.N. Ngyuen, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 11818 11819
23. V. Percec, G.M. Golding, J. Smidrkal, and O. Weichold J. Org. Chem. 69 2004 3447 3452
24. V. Percec, J.-Y. Bae, and D.H. Hill J. Org. Chem. 60 1995 1060 1065
25. Suzuki-Miyaura coupling reactions involving aryl mesylates: V. Percec, J.-Y. Bae, M. Zhao, and D.H. Hill J. Org. Chem. 60 1995 1066 1069 Also see Refs. 5 and 8
26. Suzuki-Miyaura coupling reactions involving vinyl tosylates: J. Wu, Q. Zhu, L. Wang, R. Fathi, and Z. Yang J. Org. Chem. 68 2003 670 673
27. J. Wu, L. Wang, R. Fathi, and Z. Yang Tetrahedron Lett. 43 2002 4395 4397
28. M.A. Huffman, and N. Yasuda Synlett 1999 471 473
29. For other coupling reactions involving aryl arenesulfonates: A.H. Roy, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 8704 8705
30. X. Huang, K.W. Anderson, D. Zim, L. Jiang, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 6653 6655
31. D. Gelman, and S.L. Buchwald Angew. Chem., Int. Ed. 42 2003 5993 5996
32. J. Wu, Y. Liao, and Z. Yang J. Org. Chem. 68 2003 3642 3645
33. A. Furstner, A. Leitner, M. Mendez, and H. Krause J. Am. Chem. Soc. 124 2002 13856 13863
34. C. Bolm, J.P. Hildebrand, and J. Rudolph Synthesis 2000 911
35. B.C. Hamann, and J.F. Hartwig J. Am. Chem. Soc. 120 1998 7369 7370
36. F. Nagatsugi, K. Uemura, S. Nakashima, M. Minoru, and S. Sasaki Tetrahedron Lett. 36 1995 421 423
37. D. Badone, R. Cecchi, and U. Guzzi J. Org. Chem. 57 1992 6321 6323
38. Z.-Y. Tang, and Q.-S. Hu J. Am. Chem. Soc. 126 2004 3058 3059
39. Z.-Y. Tang, Y. Lu, and Q.-S. Hu Org. Lett. 5 2003 297 300
40. Recent reviews: W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290 1300
41. A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang, and S.P. Nolan J. Organomet. Chem. 653 2002 69 82