Rapid synthesis of an electron-deficient t-BuPHOX ligand: Cross-coupling of aryl bromides with secondary phosphine oxides

Tetrahedron Letters

Volumn 51, Issue 42, 2010, Pages 5550-5554

  McDougal, Nolan T ^a   Streuff, Jan ^a   Mukherjee, Herschel ^a   Virgil, Scott C ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; COPPER; LIGAND; OXAZOLINE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHINOOXAZOLINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 77956647486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.039     Document Type: Article

References (45)

1. For reviews, see: H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151 4202
2. G.C. Hargaden, and P.J. Guiry Chem. Rev. 109 2009 2505 2550
3. P. von Matt, and A. Pfaltz Angew. Chem., Int. Ed. Engl. 32 1993 566 568
4. J. Sprinz, and G. Helmchen Tetrahedron Lett. 34 1993 1769 1772
5. G.J. Dawson, C.G. Frost, J.M.J. Williams, and S.J. Coote Tetrahedron Lett. 34 1993 3149 3150
6. For a review, see: G. Helmchen, and A. Pfaltz Acc. Chem. Res. 33 2000 336 345
7. See also: A. Pfaltz Acta Chem. Scand. B 50 1996 189 194
8. J.M.J. Williams Synlett 1996 705 710
9. G. Helmchen, S. Kudis, P. Sennhenn, and H. Steinhagen Pure Appl. Chem. 69 1997 513 518
10. For selected examples of the use of t-BuPHOX in asymmetric reactions, see: O. Loiseleur, P. Meier, and A. Pfaltz Angew. Chem., Int. Ed. 35 1996 200 202
11. L. Ripa, and A. Hallberg J. Org. Chem. 62 1997 595 602
12. I. Sagasser, and G. Helmchen Tetrahedron Lett. 39 1998 261 264
13. O. Loiseleur, M. Hayashi, M. Keenan, N. Schmees, and A. Pfaltz J. Organomet. Chem. 576 1999 16 22
14. P. Nilsson, H. Gold, M. Larhed, and A. Hallberg Synthesis 2002 1611 1614
15. K. Hiroi, and W. Kazuhiro Tetrahedron: Asymmetry 13 2002 1841 1843
16. S.R. Schulz, and S. Blechert Angew. Chem., Int. Ed. 46 2007 3966 3970
17. M.J. Cook, and T. Rovis J. Am. Chem. Soc. 129 2007 9302 9303
18. E. Linton, and M.C. Kozlowski J. Am. Chem. Soc. 130 2008 16162 16163
19. D.C. Behenna, and B.M. Stoltz J. Am. Chem. Soc. 126 2004 15044 15045
20. J.T. Mohr, D.C. Behenna, A.M. Harned, and B.M. Stoltz Angew. Chem., Int. Ed. 44 2005 6924 6927
21. M. Seto, J.L. Roizen, and B.M. Stoltz Angew. Chem., Int. Ed. 47 2008 6873 6876
22. J.T. Mohr, T. Nishimata, D.C. Behenna, and B.M. Stoltz J. Am. Chem. Soc. 128 2006 11348 11349
23. S.C. Marinescu, T. Nishimata, J.T. Mohr, and B.M. Stoltz Org. Lett. 10 2008 1039 1042
24. K. Tani, D.C. Behenna, R.M. McFadden, and B.M. Stoltz Org. Lett. 9 2007 2529 2531
25. D.E. White, I.C. Stewart, R.H. Grubbs, and B.M. Stoltz J. Am. Chem. Soc. 130 2008 810 811
26. J. Streuff, D.E. White, S.C. Virgil, and B.M. Stoltz Nat. Chem. 2 2010 192 196
27. M.R. Krout, J.T. Mohr, and B.M. Stoltz Org. Synth. 86 2009 181 193
28. D. Gelman, L. Jiang, and S.L. Buchwald Org. Lett. 5 2003 2315 2318
29. C.A. Busacca, J.C. Lorenz, N. Grinberg, N. Haddad, M. Hrapchak, B. Latli, H. Lee, P. Sabila, A. Saha, M. Sarvestani, S. Shen, R. Varsolona, X. Wei, and C.H. Senanayake Org. Lett. 7 2005 4277 4280
30. C.A. Busacca, J.C. Lorenz, P. Sabila, N. Haddad, and C.H. Senanyake Org. Synth. 84 2007 242 261
31. For Pd-catalyzed couplings of secondary phosphine oxides with aryl halides and aryl triflates, see: Y. Xu, Z. Li, J. Xia, H. Guo, and Y. Huang Synthesis 1984 781 782
32. Y. Uozumi, A. Tanahashi, S.-Y. Lee, and T. Hayashi J. Org. Chem. 58 1993 1945 1948
33. M.M. Kabachnik, M.D. Solntseva, and I.P. Beletskaya Russ. Chem. Bull. 46 1997 1491
34. M. Toffano, C. Dobrota, and J.-C. Fiaud Eur. J. Org. Chem. 2006 650 656
35. For Cu-catalyzed couplings of secondary phoshine oxides with aryl halides, see: H. Rao, Y. Jin, H. Fu, Y. Jiang, and Y. Zhao Chem. Eur. J. 12 2006 3636 3646
36. C. Huang, X. Tang, H. Fu, Y. Jiang, and Y. Zhao J. Org. Chem. 71 2006 5020 5022
37. D. Jiang, Q. Jiang, H. Fu, Y. Jiang, and Y. Zhao Synthesis 2008 3473 3477
38. 10
39. 9
40. M. Grayson, C.E. Farley, and C.A. Streuli Tetrahedron 23 1967 1065 1078
41. J.L. Leazer Jr., R. Cvetovich, F.-R. Tsay, U. Dolling, T. Vickery, and D. Bachert J. Org. Chem. 68 2003 3695 3698
42. +: 339.0373, found 339.0387.
43. 2).
44. G. Koch, G.C. Lloyd-Jones, O. Loiseleur, A. Pfaltz, R. Pretot, S. Schaffner, P. Schnider, and P. von Matt Recl. Trav. Chim. Pays-Bas 114 1995 206 210
45. 9,10