Pd2dba3/P(i-BuNCH2CH2) 3N: A highly efficient catalyst for the one-pot synthesis of trans-4-N,N-diarylaminostilbenes and N,N-diarylaminostyrenes

Tetrahedron

Volumn 61, Issue 41, 2005, Pages 9775-9782

  Nandakumar, Mecheril V ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Amination; C C Coupling; Heck reaction; Palladium; Proazaphosphatranes; Trans 4 N,N, Diarylaminostilbenes

Indexed keywords

CARBON; CHLORIDE; HALIDE; HYDROGEN; NITROGEN; PALLADIUM; STILBENE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; MOLECULE; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 24344441594     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.117     Document Type: Article

References (45)

1. For general references see; (a) J. Tsuji Palladium Reagents and Catalysis: Innovations In Organic Synthesis 1995 Wiley Chichester, England
2. E.I. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1-2 2002 Wiley New York
3. P.P. Deshpande, and O.R. Martin Tetrahedron Lett. 31 1990 6313 6316
4. T. Matsumoto, T. Hosoya, and K. Suzuki J. Am. Chem. Soc. 114 1992 3568 3570
5. M. Kitamura, K. Ohmori, T. Kawase, and K. Suzuki Angew. Chem., Int. Ed. 38 1999 1229 1232
6. Proazaphosphatranes such as 1 are commercially available (Aldrich, Strem and Digital Specialty Chemicals).
7. P.B. Kisanga, and J.G. Verkade Tetrahedron 57 2001 467 475
8. S. Urgaonkar, M. Nagarajan, and J.G. Verkade J. Org. Chem. 68 2003 452 459
9. S. Urgaonkar, M. Nagarajan, and J.G. Verkade Org. Lett. 5 2003 815 818
10. S. Urgaonkar, M. Nagarajan, and J.G. Verkade Tetrahedron Lett. 43 2002 8921 8924
11. W. Su, S. Urgaonkar, and J.G. Verkade Org. Lett. 6 2004 1421 1424
12. W. Su, S. Urgaonkar, and J.G. Verkade J. Am. Chem. Soc. 126 2004 16433 16439
13. For recent reviews, see: (a) J.G. Verkade Top. Curr. Chem. 233 2002 1
14. J.G. Verkade, and P.B. Kisanga Aldrichim. Acta 37 2004 3 14
15. J.G. Verkade, and P.B. Kisanga Tetrahedron 59 2003 7819 7853
16. S.D. Edmondson, A. Mastraechio, and E.R. Parmee Org. Lett. 2 2000 1109 1112
17. P. Matyus, B.U.W. Maes, Z. Riedl, G. Hajos, L.F. Lemiere, P. Tapolcsanyi, K. Monsieurs, O. Elias, R.A. Dommisse, and G. Krajsovszky Synlett 7 2004 1123 1139
18. G. Cuny, M.B. Choussy, and J. Zgu Angew. Chem., Int. Ed. 42 2003 4774 4777
19. V. Khedkar, A. Tillack, M. Michalik, and M. Beller Tetrahedron Lett. 45 2004 3123 3126
20. H. Siebeneicher, I. Bytschkov, and S. Doye Angew. Chem., Int. Ed. 42 2003 3042 3044
21. K. Yamazaki, Y. Nakamura, and Y. Kondo J. Chem. Soc., Perkin Trans. 1 2002 2137 2138
22. R. Lira, and J.P. Wolfe J. Am. Chem. Soc. 126 2004 13906 13907
23. (a) Sasaki, M. (Ricoh Co., Ltd Japan). Ger. Offen. Patent Application DE 83-3315437 19830428, 1983, 97; Chem. Abstr. No. 100, 112236.
24. Y. Oda, T. Homma, and F. Yoshihide Denshi Shashin Gakkaishi 29 1990 250 258
25. Y. Fujimaki, H. Tadokoro, Y. Oda, H. Yoshioka, T. Homma, H. Moriguchi, K. Watanabe, A. Konishita, and N. Hirose J. Imaging Technol. 17 1991 202 206
26. J.S. Yang, S.Y. Chiou, and K.L. Lia J. Am. Chem. Soc. 124 2002 2518 2527
27. J.S. Yang, Y.H. Lin, and C.S. Yang Org. Lett. 4 2002 777 780
28. X.D. Cao, X.Q. Zhou, Q.M. Dong, Q. He, and D.Z. Liu Jingxi Huagong 20 2003 452 454
29. S. Sengupta, S.K. Sadhukaran, and S. Muhuri Tetrahedron Lett. 43 2002 3521 3524
30. T.C. Lin, G.S. He, P.N. Prasad, and L.S. Tan J. Mater. Chem. 14 2004 982 991
31. M.V. Nandakumar, and J.G. Verkade Angew. Chem., Int. Ed. 44 2005 3115 3118
32. (a) Sasaki, M. Ger. Offen. Patent Application. DE 3342724A1-19840530, 1984, Chem. Abstr. No. 101, 219792.
33. A.S. Gajare, K. Toyota, M. Yoshifuji, and F. Ozawa Chem. Commun. 17 2004 1994 1995
34. H.J. Lee, J. Sohn, J. Hwang, S.Y. Park, H. Choi, and M. Cha Chem. Mater. 3 2004 456 465
35. (a) Fujimaki, Y.; Suzuki, Y.; Takei, Y.; Nomori, H. (Konishiroku Photo Industry Co. Ltd Japan). Jpn. Kokai Tokkyo Application JP 84-69481 19840407, 1985; Chem. Abstr. No. 104, 159589.
36. P.M. Borsenberger, J.R. Cowdery-Corvan, E.H. Magin, and J.A. Sinicropi Thin Solid Films 307 1997 215 220
37. M. Behl, E. Hattemer, and M. Brehmer Macrmol. Chem. Phys. 203 2002 503 510
38. S.M. Lindner, and M. Thelakkat Macromolecules 37 2004 8832 8835
39. (b) Shoichi, N.; Hisao, E. (Tosoh Corpn., Japan) Jpn. Kokai Tokkyo Patent No. JP 2002-80870 20020322, 2003, Chem. Abstr. No. 139 276694.
40. C.L. Li, S.J. Shieh, S.C. Lin, and R.S. Liu Org. Lett. 5 2003 1131 1134
41. (a) Sato, Y.; Okata, T.; Ichinosawa, A. (Mitsubishi Chemical Industries Ltd, Japan). Jpn. Kokai Tokkyo Koho Patent No. 2000150169, 2000, Chem. Abstr. No.133, 10852.
42. (b) Sage, I. C.; Wood, E. L.; Feast, W. J.; Peace, R. J. Crit. UK Pat. Appl Patent No. GB 2334959, 1999, Abstr. No.132, 23286.
43. T. Ohta, S. Miyake, and K. Shudo Tetrahedron Lett. 26 1985 5811 5814
44. V. Collot, P.R. Bovy, and S. Rault Tetrahedron Lett. 41 2000 9053 9057
45. J.P. Wolfe, R.A. Rennels, and S.L. Buchwald Tetrahedron 52 1996 7525 7546