Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant

Journal of Organometallic Chemistry

Volumn 696, Issue 1, 2011, Pages 46-49

  Xu, Tao ^a   Qiu, Shuifa ^a   Liu, Guosheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alcohol oxidation; Hydroamination; Palladium; Styrene

Indexed keywords

ALCOHOL OXIDATION; BATHOCUPROINE; HYDROAMINATIONS; INTRAMOLECULAR HYDROAMINATION; NITROGEN LIGAND; NITROGEN SOURCES; OXIDATIVE CONDITIONS;

CATALYSIS; FLUORINE; OXIDANTS; PALLADIUM; STYRENE;

OXIDATION;

EID: 78649810964     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.07.015     Document Type: Article

References (62)

1. For recent reviews, see:
2. T.E. Müller, and M. Beller Chem. Rev. 98 1998 675
3. J.J. Brunet, and D. Neibecker Catalytic Heterofunction-Alization 2001 Wiley-VCH Weinheim 91 141
4. K.C. Hultzsch Adv. Synth. Catal. 347 2005 367
5. T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo, and M. Tada Chem. Rev. 108 2008 3795
6. S. Hong, and T.J. Marks Acc. Chem. Res. 37 2004 673
7. Y.K. Kim, T. Livinghouse, and Y. Horino J. Am. Chem. Soc. 125 2003 9560
8. J.S. Ryu, G.Y. Li, and T.J. Marks J. Am. Chem. Soc. 125 2003 12584
9. G.A. Molander, and E.D. Dowdy J. Org. Chem. 63 1998 8983
10. L. Ackermann, R.G. Bergman, and R.N. Loy J. Am. Chem. Soc. 125 2003 11956
11. D.V. Gribkov, and K.C. Hultzsch Angew. Chem. Int. Ed. 43 2004 5542
12. I. Bytschkov, and S. Doye Eur. J. Org. Chem. 88 2003 935
13. P.D. Knight, I. Munslow, P.N. O'Shaughnessy, and P. Scott Chem. Commun. 2004 894
14. J.A. Bexrud, J.D. Beard, D.C. Leitch, and L.L. Schafer Org. Lett. 7 2005 1959
15. M. Utsunomiya, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 14286
16. A. Takemiya, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 6042
17. M. Utsunomiya, R. Kuwano, M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 5608
18. N. Sakai, A. Ridder, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 8134
19. For some reviews and selective examples, see:
20. S. Ma Chem. Rev. 105 2005 2829
21. R. Zimmer, C.U. Dinesh, E. Nandanan, and F.A. Khan Chem. Rev. 100 2000 3067
22. C.F. Bender, and R.A. Widenhoefer Chem. Commun. 2006 4143
23. C. Brouwer, and C. He Angew. Chem. Int. Ed. 45 2006 1744
24. G.L. Hamilton, E.J. Kang, M. Mba, and F.D. Toste Science 317 2007 496
25. K. Komeyama, T. Morimoto, and K. Takaki Angew. Chem. Int. Ed. 45 2006 2938
26. Z. Zhang, C. Liu, R.E. Kinder, X. Han, H. Qian, and R.A. Widenhoefer J. Am. Chem. Soc. 128 2006 9066
27. Few cases of palladium(II)-catalyzed hydroamination of alkenes with pincer ligand were reported recently, see:
28. F.E. Michael, and B.M. Cochran J. Am. Chem. Soc. 128 2006 4246
29. B.M. Cochran, and F.E. Michael J. Am. Chem. Soc. 130 2008 2786
30. S.S. Stahl Angew. Chem. Int. Ed. 43 2004 3400
31. F. Fache, E. Schulz, M.L. Tommasino, and M. Lemaire Chem. Rev. 100 2000 2159
32. L.M. Rendina, and R.J. Puddephatt Chem. Rev. 97 1997 1735
33. The selective examples for the late transition metal-catalyzed hydroamination of alkyne using nitrogen-based ligands, see:
34. S. Burling, L.D. Field, B.A. Messerle, and P. Turner Organometallics 23 2004 1714
35. L.D. Field, B.A. Messerle, and S.L. Wren Organometallics 22 2003 4393
36. S. Burling, L.D. Field, and B.A. Messerle Organometallics 19 2000 87
37. Some examples of palladium-catalyzed oxidation reactions using bathocuproine as the ancillary ligand, see:
38. S.S. Stahl, J.L. Thorman, R.C. Nelson, and M.A. Kozee J. Am. Chem. Soc. 123 2001 7188
39. D. Bianchi, R. Bortolo, R. D'Aloisio, and M. Ricci Angew. Chem. Int. Ed. 38 1999 706
40. S. Qiu, Y. Wei, and G. Liu Chem. Eur. J. 15 2009 2751
41. Recent mechanistic studies demonstrated that the cis-aminopalladation is favoured in the palladium catalyzed oxidative amination of alkenes. It means that the coordination between amide and palladium is existence, see:
42. J.L. Brice, J.E. Harang, V.I. Timokhin, N.R. Anastasi, and S.S. Stahl J. Am. Chem. Soc. 127 2005 2868
43. G. Liu, and S.S. Stahl J. Am. Chem. Soc. 128 2006 7179
44. G. Liu, and S.S. Stahl J. Am. Chem. Soc. 129 2007 6328
45. K. Muñiz, C.H. Hövelmann, and J. Streuff J. Am. Chem. Soc. 130 2008 763
46. For discussion of palladium-mediated aerobic oxidation was inhibited by HOAc, see: B.A. Steinhoff, I.A. Guzei, and S.S. Stahl J. Am. Chem. Soc. 126 2004 11268
47. D. Kalyani, A.R. Dick, W.Q. Anani, and M.S. Sanford Org. Lett. 8 2006 2523
48. S.R. Whitfield, and M.S. Sanford J. Am. Chem. Soc. 129 2007 15142
49. F.E. Michael, P.A. Sibbald, and B.M. Cochran Org. Lett. 10 2008 793
50. P.A. Sibbald, and F.E. Michael Org. Lett. 11 2009 1147
51. II-H species, see:
52. K.M. Gligorich, S.A. Cummings, and M.S. Sigman J. Am. Chem. Soc. 129 2007 14193
53. Y. Iwai, K.M. Gligorich, and M.S. Sigman Angew. Chem. Int. Ed. 47 2008 3219 For the reaction of conjugated diene insertion into Ir or Ru-H species, see
54. F. Shibahara, J.F. Bower, and M.J. Krische J. Am. Chem. Soc. 130 2008 6338
55. J.F. Bower, R.L. Patman, and M.J. Krische Org. Lett. 10 2008 1033
56. The reactions using 1 and NCS as nitrogen source afforded alkoxy-chlorination products in moderate yields, see P.A. Bentley, Y. Mei, and J. Du Tetrahedron Lett. 49 2008 2653
57. For palladium-catalyzed aminofluorination of styrenes, see: S. Qiu, T. Xu, J. Zhou, Y. Guo, and G. Liu J. Am. Chem. Soc. 132 2010 2856
58. 0 to HX, see:
59. J.F. Hartwig Pure Appl. Chem. 76 2004 507 and reference therein
60. M. Meguro, and Y. Yamamoto Tetrahedron Lett. 39 1998 5421
61. A byproduct was obtained, but its structure cannot be characterized currently.
62. For the oxidation of Pd(II) to Pd(IV) by NFSI, see: P.A. Sibbald, C.F. Rosewall, R.D. Swartz, and F.E. Michael J. Am. Chem. Soc. 131 2009 15945