Synthesis of C2-symmetric and unsymmetrically substituted 2,2′-dipyridylamines and crystal structure of a chiral 2,2′-dipyridylamine copper(II) complex

Journal of Organometallic Chemistry

Volumn 689, Issue 23, 2004, Pages 3767-3777

  Bolm, Carsten ^a   Frison, Jean Cédric ^a   Paih, Jacques Le ^a   Moessner, Christian ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

2,2 Dipyridylamines; Allylic oxidation; Catalysis; N Arylation reactions; Palladium

Indexed keywords

CATALYSIS; COMPLEXATION; COPPER COMPOUNDS; CRYSTAL STRUCTURE; OXIDATION; PALLADIUM; X RAY ANALYSIS;

2,2́-DIPYRIDYLAMINES; ALLYLIC OXIDATION; N-ARYLATION REACTIONS;

ORGANIC COMPOUNDS;

EID: 19344370563     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.06.032     Document Type: Article

References (51)

1. F. Fache, E. Schulz, M. Tommasino, and M. Lemaire Chem. Rev. 100 2000 2159
2. C. Bolm R.W. Hoffmann K.H. Dötz Advances in Organic Synthesis via Organometallics 1991 Vieweg Verlag Wiesbaden 223
3. G. Chelucci, and R.P. Thummel Chem. Rev. 102 2002 3129
4. N.C. Fletcher J. Chem. Soc., Perkin Trans. 1 2002 1831
5. A.V. Malkov, and P. Kocovsky Curr. Org. Chem. 7 2003 1737
6. M.E. Wright, S.A. Svejda, M.J. Jin, and M.A. Peterson Organometallics 9 1990 136
7. G. Chelucci, G. Loriga, G. Murineddu, and G.A. Pinna Tetrahedron Lett. 43 2002 8599
8. For an earlier example of chiral dipyridylmethane see: C. Moberg, and K. Wärnmark J. Org. Chem. 56 1991 3339
9. H.-L. Kwong, L.-S. Cheng, W.-S. Lee, W.-L. Wong, and W.-T. Wing Eur. J. Inorg. Chem. 2000 1997
10. T. Schareina, G. Hildebrand, H. Fuhrmann, and R. Kempe Eur. J. Inorg. Chem. 2001 2421
11. J. Silberg, T. Schareina, R. Kempe, K. Wurst, and M.R. Buchmeiser J. Organomet. Chem. 622 2001 6
12. For examples, see: D. Miao, Y.-M. Guo, S.T. Chen, X.-H. Bu, and J. Ribas Inorg. Chim. Acta 346 2003 207
13. P. de Hoog, P. Gamez, O. Roubeau, M. Lutz, W.L. Driessen, A.L. Spek, and J. Reedijk New J. Chem. 27 2003 18
14. S. Youngme, G.A. van Albada, O. Roubeau, C. Pakawatchai, N. Chaichit, and J. Reedijk Inorg. Chim. Acta 342 2003 48
15. J. Carranza, C. Brennan, J. Sletten, F. Lloret, and M. Julve J. Chem. Soc., Dalton Trans. 2002 3164
16. S. Youngme, N. Chaichit, and K. Damnatara Polyhedron 21 2002 943
17. S. Youngme, N. Chaichit, P. Kongsaeree, G.A. van Albada, and J. Reedijk Inorg. Chim. Acta 324 2001 232
18. L. Song, and W.C. Trogler J. Organomet. Chem. 452 1993 271
19. J.S. Thompson, and R.M. Swiatek Inorg. Chem. 24 1985 110
20. B.H. Yang, and S.L. Buchwald J. Organomet. Chem. 576 1999 125
21. J.F. Hartwig E.-I. Negishi A. de Meijere Handbook of Organopalladium Chemistry for Organic Synthesis vol. 1 2002 Wiley VCH 1051
22. S. Wagaw, and S.L. Buchwald J. Org. Chem. 61 1996 7240
23. C. Bolm, J.-C. Frison, J. Le Paih, and C. Moessner Tetrahedron Lett. 45 2004 5019
24. C. Bolm, M. Ewald, M. Felder, and G. Schlingloff Chem. Ber. 125 1992 1169 and references therein
25. C. Bolm, and J.P. Hildebrand Tetrahedron Lett. 39 1998 5731
26. C. Bolm, and J.P. Hildebrand J. Org. Chem. 65 2000 169
27. C. Bolm, J.P. Hildebrand, and J. Rudolph Synthesis 2000 911
28. General reviews on sulfoximines: C.R. Johnson Acc. Chem. Res. 6 1973 341
29. S. Pyne Sulfur Reports 12 1992 57
30. M. Reggelin, and C. Zur Synthesis 2000 1
31. For the application of sulfoximines in asymmetric metal catalysis, see: M. Harmata Chemtracts 16 2003 660
32. H. Okamura, and C. Bolm Chem. Lett. 6 2004 1305
33. D. Cai, D.L. Hughes, and T. Verhoeven Tetrahedron Lett. 37 1996 2537
34. R.H. Dodd, and M. Le Hyaric Synthesis 1995 295
35. A.V. Malkov, M. Bella, V. Langer, and P. Kocovsky Org. Lett. 2 2000 3047
36. A.V. Malkov, I.R. Baxendale, M. Bella, V. Langer, J. Fawcett, D.R. Russell, D.J. Mansfield, M. Valko, and P. Kocovsky Organometallics 20 2001 673
37. Ru(II): M. Haukka, P. Da Costa, and S. Luukkanen Organometallics 22 2003 5137
38. Ir(I) and Rh(I): L.A. Oro, M.A. Ciriano, and F. Viguri Inorg. Chim. Acta 115 1986 65
39. J. Yin, and S.L. Buchwald Org. Lett. 2 2000 1101
40. G. Mann, J.F. Hartwig, M.S. Driver, and C. Fernández-Rivas J. Am. Chem. Soc. 120 1998 827
41. J.P. Wolfe, J. Ahman, J.P. Sadighi, R.A. Singer, and S.L. Buchwald Tetrahedron Lett. 38 1997 6367
42. X. Huang, and S.L. Buchwald Org. Lett. 3 2001 3417
43. For the effect of bromide on the reaction rate, see: L.M. Alcazar-Roman, and J.F. Hartwig J. Am. Chem. Soc. 123 2001 12905
44. For halide effects in catalyses, see: C. Amatore, and A. Jutand Acc. Chem. Res. 33 2000 314
45. K. Fagnou, and M. Lautens Angew. Chem. Int. Ed. 41 2000 26
46. For an achiral analogue, see: S.P. Foxon, O. Walter, and S. Schindler Eur. J. Inorg. Chem. 2002 111
47. C. Harris, O. Geis, and S.L. Buchwald J. Org. Chem. 64 1999 6019
48. S. Kirschner Inorg. Synth. 5 1957 14
49. E. Spodine, A.M. Atria, R. Baggio, and M.T. Garland Acta Cryst.C 52 1996 1407
50. M.B. Andrus, and J.C. Lashley Tetrahedron 58 2002 845
51. G. Schlingloff, and C. Bolm M. Beller C. Bolm Transition Metals For Organic Chemistry vol. 2 1998 Wiley/VCH Weinheim 193