Chiral tetradentate amine and tridentate aminocarbene ligands: Synthesis, reactivity and X-ray structural characterizations

Inorganica Chimica Acta

Volumn 359, Issue 14, 2006, Pages 4549-4556

  Michon, Christophe ^a   Ellern, Arkady ^a   Angelici, Robert J ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Copper(I); Heck reaction; Palladium(II); Tetradentate amine; Tridentate aminocarbene

Indexed keywords

AMINES; CHELATION; COPPER COMPOUNDS; ORGANOMETALLICS; STYRENE;

COPPER (I) COMPLEXES; HECK REACTIONS; HOMOGENEOUS CATALYST; PALLADIUM ACETATE; PALLADIUM COMPLEXES; STRUCTURAL CHARACTERIZATION; TETRADENTATE; TRIDENTATE AMINOCARBENE;

PALLADIUM COMPOUNDS;

EID: 33748530650     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2006.07.019     Document Type: Article

References (58)

1. Öfele K. J. Organomet. Chem. 12 (1968) P42
2. Wanzlick H.W., and Schonher H.J. Angew. Chem., Int. Ed. 7 (1968) 141
3. Cardin D.J., Cetinkaya B., Cetinkaya E., Lappert M.F., Randall E.W., and Rosenber E. J. Chem. Soc., Dalton Trans. (1973) 1982
4. Arduengo III A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
5. Scott N.M., and Nolan S.P. Eur. J. Inorg. Chem. (2005) 1815
6. Peris E., and Crabtree R.H. Coordin. Chem. Rev. 248 (2004) 2239
7. Crudden C.M., and Allen D.P. Coordin. Chem. Rev. 248 (2004) 2247
8. Grubbs R.H. Tetrahedron 60 (2004) 7117
9. Hoveyda A.H., and Schrock R.R. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Supplement (2004), Springer-Verlag, Berlin, Germany 207-233
10. Michon C., and Angelici R.J. ChemTracts 17 (2004) 534
11. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
12. Herrmann W.A., Weskamp T., and Böhm V.P.W. Adv. Organomet. Chem. 48 (2002) 1
13. Bourissou D., Guerret O., Gabbai{dotless}̈ F., and Bertrand G. Chem. Rev. 100 (2000) 39
14. For reviews:. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
15. César V., Bellemin-Laponnaz S., and Gade L.H. Chem. Soc. Rev. 33 (2004) 619
16. For some representative examples: Hydrogenation:. Bappert E., and Helmchen G. Synlett (2004) 1789
17. Focken T., Raabe G., and Bolm C. Tetrahedron: Asymmetry 15 (2004) 1693
18. Perry M.C., Cui X., Powell M.T., Hou R.-R., Reibenspies J.H., and Burgess K.J. J. Am. Chem. Soc. 125 (2003) 113
19. Seo H., Park H.J., Kim B.Y., Lee J.H., Son S.U., and Chung Y.K. Organometallics 22 (2003) 618
20. Hydrosilylation:. Gade L.H., César V., and Bellemin-Laponnaz S. Angew. Chem., Int. Ed. 43 (2004) 1014
21. Duan W.L., Shi M., and Rong G.B. Chem. Commun. (2003) 2916
22. Enders D., and Gielen H. J. Organomet. Chem. 617 (2001) 70
23. Herrmann W.A., Goossen L.J., Köcher C., and Artus G.R.J. Angew. Chem., Int. Ed. 35 (1996) 2805
24. Conjugate additions of arylboronic acids:. Ma Y., Song C., Ma C., Sun Z., Chai Q., and Andrus M.B. Angew. Chem., Int. Ed. 42 (2003) 5871
25. Becht J.M., Bappert E., and Helmchen G. Adv. Synth. Catal. 347 (2005) 1495
26. Hydroamination. Gishig S., and Togni A. Organometallics 23 (2004) 2479
27. Conjugate additions of organozinc reagents to enones:. Guillen F., Winn C.L., and Alexakis A. Tetrahedron: Asymmetry 12 (2001) 2083
28. Pytkowicz J., Roland S., and Mangeney P. Tetrahedron Asymmetry 12 (2001) 2087
29. Cross-coupling reactions:. Glorius F., Altenhoff G., Goddard R., and Lehmann C. Chem. Commun. 22 (2002) 2704
30. Seiders T.J., Ward D.W., and Grubbs R.H. Org. Lett. 3 (2001) 3225
31. Funk T.W., Berlin J.M., and Grubbs R.H. J. Am. Chem. Soc. 128 (2006) 1840
32. For an overview:. Desimoni G., Faita G., and Quadrelli P. Chem. Rev. 103 (2003) 3119
33. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805
34. Hartwig J.F. Acc. Chem. Res. 31 (1998) 852
35. Cabanal-Duvillard I., and Mageney P. Tetrahedron Lett. 40 (1999) 3877
36. Jensen K.A., and Nielsen P.H. Acta Chem. Scand. 18 (1964) 1
37. Nielsen P.H., and Dahl O. Acta Chem. Scand. 20 (1966) 1113
38. Suzuki T.M., Kamiyama S., and Kimura T. Bull. Chem. Soc. Jpn. 51 (1978) 1094
39. Suzuki T.M., Ohba S., Sato S., Saito Y., and Saito K. Inorg. Chem. 22 (1983) 2048
40. Ribas J., Diaz C., and Casabo J. Polyhedron 3 (1984) 357
41. Jones P., Vagg R.S., and Williams P.A. Inorg. Chem. 23 (1984) 4110
42. Jones P., Williams P.A., and Vagg R.S. Inorg. Chim. Acta 103 (1985) 49
43. Ribas J., Diaz C., Monfort M., Corbella M., Solans X., and Font-Altaba M. Inorg. Chim. Acta 117 (1986) 49
44. Diaz C., and Ribas J. Polyhedron 11 (1992) 85
45. Okada T., Yoshida M., Hirose T., Kasuga K., Yu T., Yuasa M., and Sekine I. Electrochim. Acta 45 (2000) 4419
46. Endres H., Keller H.J., and Poveda A. Z. Naturforsch. B: Chem. Sci. 32 (1977) 131
47. Ohrai K., Kondo K., Sodeoka M., and Shibasaki M. J. Am. Chem. Soc. 116 (1994) 11737
48. Amatore C., Jutand A., and M'Barki M.A. Organometallics 11 (1992) 3009
49. Ozawa F., Kubo A., Matsumoto Y., and Hayashi T. Organometallics 12 (1993) 4188
50. Shibasaki M., and Vogl E.M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Supplement (2004), Springer-Verlag, Berlin, Germany 73-81
51. Bedford R.B., Cazin C.S.J., and Holder D. Coordin. Chem. Rev. 248 (2004) 2283
52. Dupont J., Consorti C.S., and Spencer J. Chem. Rev. 105 (2005) 2527
53. Miyazaki F., Yamaguchi K., and Shibasaki M. Tetrahedron Lett. 40 (1999) 7379
54. Huang M.H., and Liang L.C. Organometallics 23 (2004) 2813
55. Takenaka K., and Uozumi Y. Adv. Synth. Catal. 346 (2004) 1693
56. Jurkauskas V., Sadighi J.P., and Buchwald S.L. Org. Lett. 5 (2003) 2417
57. Kaur H., Zinn F.K., Stevens E.D., and Nolan S.P. Organometallics 23 (2004) 1157
58. Di{dotless}́ez-González S., Kaur H., Zinn F.K., Stevens E.D., and Nolan S.P. J. Org. Chem. 70 (2005) 4784