Pd-catalyzed Negishi coupling of pyrazole triflates with alkyl zinc halides

Tetrahedron Letters

Volumn 52, Issue 2, 2011, Pages 311-313

  Zhang, Ting ^a   Gao, Xiaodi ^b   Wood, Harold B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Analog synthesis; Cross coupling; Negishi coupling; Organozinc reagents; Palladium catalysis; Pyrazole triflates

Indexed keywords

ALKYL ZINC HALIDE DERIVATIVE; HALIDE; PALLADIUM; PYRAZOLE DERIVATIVE; PYRAZOLE TRIFLATE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; NEGISHI COUPLING;

EID: 78650025421     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.037     Document Type: Article

References (39)

1. J.A. Joule, and K. Mills Heterocyclic Chemistry 5th ed. 2009 Wiley UK pp 494
2. Alternatively, 3-substituted pyrazoles can be accessed via ortho-lithiation-alkylation methods from unsubstituted pyrazoles, see: E. Diez-Barra, A. de la Hoz, A. Sanchez-Migallon, and J. Tejeda J. Chem. Soc., Perkin Trans. 1: Org. Bio.-Org. Chem. 9 1993 1079
3. Sore, H. F.; Boyle, R. G.; Hamlett, C.; Saxty, G.; Verdonk, M. L.; Walker, D. W.; Woodhead, S. J.; Howard, S. WO Patent 2006136829, 2006.
4. Pelcman, B.; Sanin, A.; Nilsson, P.; Boesen, T.; Vogensen, S. B.; Kromann, H.; Groth, T. WO Patent 2007045868, 2007.
5. Recent literature of Negishi coupling reactions: J.E. Milne, and S.L. Buchwald J. Am. Chem. Soc. 126 2004 13028
6. S. Sase, M. Jaric, A. Metzger, V. Malakhov, and P. Knochel J. Org. Chem. 73 2008 7380
7. Z. Xi, Y. Zhou, and W. Chen J. Org. Chem. 73 2008 8497
8. N. Hadei, E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Org. Lett. 7 2005 3805
9. C. Han, and S.L. Buchwald J. Am. Chem. Soc. 131 2009 7532
10. J. Liu, Y. Deng, H. Wang, H. Zhang, G. Yu, B. Wu, H. Zhang, Q. Li, T.B. Marder, Z. Yang, and A. Lei Org. Lett. 10 2008 2661
11. S. Son, and G.C. Fu J. Am. Chem. Soc. 130 2008 2756
12. L. Wang, and Z.-X. Wang Org. Lett. 9 2007 4335
13. S. Huo Org. Lett. 5 2003 423
14. J. Zhou, and G.C. Fu J. Am. Chem. Soc. 125 2003 12527
15. X. Luo, H. Zhang, H. Duan, Q. Liu, L. Zhu, T. Zhang, and A. Lei Org. Lett. 9 2007 4571
16. C. Wang, T. Tobrman, Z. Xu, and E.I. Negishi Org. Lett. 11 2009 4092
17. J. Zhao, Y. Liu, and S. Ma Org. Lett. 10 2008 1521
18. T. Luu, Y. Morisaki, N. Cunningham, and R.R. Tykwinski J. Org. Chem. 72 2007 9622
19. F.O. Arp, and G.C. Fu J. Am. Chem. Soc. 127 2005 10482
20. A.A. Jalil, N. Kurono, and M. Tokuda Synthesis 2002 2681
21. H. Nakatsuji, K. Ueno, T. Misaki, and Y. Tanabe Org. Lett. 10 2008 2131
22. S. Wunnderlich, and P. Knochel Org. Lett. 10 2008 4705
23. U. Kiehne, J. Bunzen, H. Staats, and A. Lutzen Synthesis 2007 1061
24. K.R. Campos, A. Klapars, J.H. Waldman, P.G. Dormer, and C.-Y. Chen J. Am. Chem. Soc. 128 2006 3538
25. X. Wang, J. Tan, and K. Grozinger Tetrahedron Lett. 41 2000 4713
26. J. Zhang, S. Didierlaurent, M. Fortin, D. Lefrancois, E. Uridat, and J.P. Vevert Bioorg. Med. Chem. Lett. 10 2000 2575
27. M.G. Organ, and S. Mayers J. Comb. Chem. 5 2003 118
28. S. Bourrain, M. Ridgill, and I. Collins Synlett 2004 795
29. C.A. Dvorak, D.A. Rudolph, S. Ma, and N.I. Carruthers J. Org. Chem. 70 2005 4188
30. J.B. Grimm, K.J. Wilson, and D.J. Witter J. Org. Chem. 74 2009 6390
31. E. Arbaciauskiene, G. Vilkauskaite, G.A. Eller, W. Holzer, and A. Sackus Tetrahedron 2009 7817
32. A.F. Littke, C. Dai, and G.C. Fu J. Am. Chem. Soc. 122 2000 4020
33. M. Rottlander, and P. Knochel J. Org. Chem. 63 1998 203
34. Pyrazole triflate 1a and nonaflate 1c were synthesized in two-steps via literature methods. Formation of pyrazolone: (a) Koenig, H.; Goetz, N.; Kirstgen, R.; Mueller, B.; Oberdorf, K.; EP Patent 680954A2, 1995
35. (b) Laggner, C.; Cuberes-Altisent, M. R.; Holenz, J.; Berrocal-Romero, J. M.; Contijoch-Llobet, M. M. WO Patent 2006021462, 2006
36. (c) Di Fabio, R.; Gentile, G.; Pozzan, A.; Tarsi, L.; Terreni, S.; Tonelli, F. WO Patent 2009130232, 2009
37. Formation of pyrazole triflates: Castro Pineiro, J. L.; Collins, I. J.; Harrison, T. U.S. Patent 2005143369, 2005
38. Formation of pyrazole nonaflates: Bourrain, S.; Ridgill, M.; Collins, I. Synlett 2004, 795.
39. All organozinc reagents were purchased from Rieke Metals as 0.5 M solutions in THF.