Preparation of planar-chiral multidonor phosphanylferrocene carboxamides and their application as ligands for palladium-catalysed asymmetric allylic alkylation

Applied Organometallic Chemistry

Volumn 24, Issue 4, 2010, Pages 326-331

  Lamač, Martin ^a   Tauchman, Jiří ^a   Dietrich, Sascha ^b   Císařová, Ivana ^a   Lang, Heinrich ^b   Štěpnička, Petr ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric allylic alkylation; Carboxamides; Ferrocene; Palladium; PAMAM; Phosphanes

Indexed keywords

ASYMMETRIC ALLYLIC ALKYLATIONS; CARBOXAMIDES; FERROCENE; FERROCENES; PHOSPHANES;

ALKYLATION; AMIDES; CARBOXYLIC ACIDS; CATALYSTS; HYDROCARBONS; IRON COMPOUNDS; LIGANDS; ORGANIC ACIDS; PALLADIUM;

ORGANOMETALLICS;

EID: 77949666677     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1616     Document Type: Article

References (69)

1. For recent reviews, see: a) A.-M. Caminade, P. Servin, R. Laurent, J.-P. Majoral, Chem. Soc. Rev. 2008, 37, 56;
2. R. Van Heerbeek, P. C. J. Kamer, P.W. N. M. Van Leeuwen, J. N. H. Reek, Chem. Rev. 2002, 102, 3717;
3. A. Berger, R. J. M. K. Gebbink, G. Van Koten, Top. Organomet. Chem. 2006, 20, 1;
4. J. K. Kassube, L. H. Gade, Top. Organomet. Chem. 2006, 20, 61;
5. B. Helms, J. M. J. Fréchet, Adv. Synth. Catal. 2006, 348, 1125;
6. D. Méry, D. Astruc, Coord. Chem. Rev. 2006, 250, 1965;
7. J. N. H. Reek, S. Arévalo, R. Van Heerbeek, P. C. J. Kamer, P.W. N. M. Van Leeuwen, Adv. Catal. 2006, 49, 71.
8. P. Štěpnička, Eur. J. Inorg. Chem. 2005, 3787; (review).
9. For recent examples, see: b) P. Štěpnička, I. Císařová, Collect. Czech. Chem. Commun. 2006, 71, 279;
10. M. Lamač, I. Císařová, P. Štěpnička, Eur. J. Inorg. Chem. 2007, 2274;
11. M. Lamač, I. Císařová, P. Štěpnička, Collect. Czech. Chem. Commun. 2007, 72, 985;
12. J. Kühnert, M. Lamač, T. Rüffer, B. Walfort, P. Štěpnička, H. Lang, J. Organomet. Chem. 2007, 692, 4303;
13. C. Bianchini, A. Meli, W. Oberhauser, A.M. Segarra, E. Passaglia, M. Lamač, P. Štěpnička, Eur. J. Inorg. Chem. 2008, 441;
14. M. Lamač, J. Cvačka, P. Štěpnička, J. Organomet. Chem. 2008, 693, 3430;
15. M. Lamač, I. Císařová, P. Štěpnička, New J. Chem. 2009, 33, 1549;
16. J. Kühnert, P. Ecorchard, H. Lang, Eur. J. Inorg. Chem. 2008, 5125.
17. D. Drahoňovský, I. Císařová, P. Štěpnička, H. Dvořáková, P. Maloň, D. Dvořák, Collect. Czech. Chem. Commun. 2001, 66, 588;
18. L. Meca, D. Dvořák, J. Ludvík, I. Císařová, P. Štěpnička, Organometallics 2004, 23, 2541;
19. P. Štěpnička, J. Schulz, I. Císař ová, K. Fejfarová, Collect. Czech. Chem. Commun. 2007, 72, 453;
20. J. Kühnert, M. Dušek, J. Demel, H. Lang, P. Štěpnička, Dalton Trans. 2007, 2802;
21. M. Lamač, J. Tauchman, I. Císařová, P. Štěpnička, Organometallics 2007, 26, 5042;
22. J. Kühnert, I. Císařová, M. Lamač, P. Štěpnička, Dalton Trans. 2008, 2454;
23. J. Tauchman, I. Císařová, P. Štepnič ka, Organometallics2009,28, 3288;
24. J. Schulz, I. Císařová, P. Ště pnička, J. Organomet. Chem. 2009, 694, 2519;
25. P. Štěpnička, M. Krupa, M. Lamač, I. Císařová, J. Organomet. Chem. 2009, 694, 2987.
26. J. Kühnert, M. Lamač, J. Demel, A. Nicolai, H. Lang, P. Štěpnička, J.Mol. Catal. A: Chem. 2008, 285, 41.
27. J. Podlaha, P. Štěpnička, J. Ludvík, I. Císařová, Organometallics1996, 15, 543.
28. D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Polym. J. 1985, 17, 117.
29. For the use of phosphane-terminated PAMAM dendrimers in catalysis, see: a) S. C. Bourque, F. Maltais, W.-J. Xiao, O. Tardif, H. Alper, P. Arya, L. E. Manzer, J. Am. Chem. Soc. 1999, 121, 3035;
30. H. Alper, P. Arya, S. C. Bourque, G. R. Jefferson, L. E. Manzer, Can. J. Chem. 2000, 78, 920;
31. A. Gong, Q. Fan, Y. Chen, H. Liu, C. Chen, F. Xi, J. Mol. Catal. A: Chem. 2000, 159, 225;
32. S. Antebi, P. Arya, L. E. Manzer, H. Alper, J. Org. Chem. 2002, 67, 6623;
33. Y. Ribourdouille, G. D. Engel, M. Richard-Plouet, L. H. Gade, Chem. Commun. 2003, 1228;
34. J. P. K. Reynhardt, H. Alper, J. Org. Chem. 2003, 68, 8353;
35. P. P. Zweni, H. Alper, Adv. Synth. Catal. 2004, 346, 849;
36. J. P. K. Reynhardt, Y. Yang, A. Sayari, H. Alper, Chem. Mater. 2004, 16, 4095;
37. R. Touzani, H. Alper, J. Mol. Catal. A: Chem. 2005, 227, 197;
38. J. P. K. Reynhardt, Y. Yang, A. Sayari, H. Alper, Adv. Synth. Catal. 2005, 347, 1379;
39. P. Li, S. Kawi, J. Catal. 2008, 257, 23;
40. J. K. Kassube, L. H. Gade, Adv. Synth. Catal. 2009, 351, 739;
41. M. Bernechea, E. De Jesus, C. Lopez-Mardomingo, P. Terreros, Inorg. Chem. 2009, 48, 4491.
42. J. M. Longmire, B. Wang, X. Zhang, Tetrahedron Lett. 2000, 41, 5435;
43. S.-L. You, X.-L. Hou, L.-X. Dai, B.-X. Cao, J. Sun, Chem. Commun. 2000, 1933;
44. P. Štěpnička, New J. Chem. 2002, 26, 567.
45. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
46. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
47. B. M. Trost, J. Org. Chem. 2004, 69, 5813;
48. T. Hayashi, Asymmetric allylic substitution and grignard cross-coupling, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), chapter 7.1, pp. 325, VCH: New York, 1993;
49. G. Helmchen, J. Organomet. Chem. 1999, 576, 203;
50. T. Hayashi, Asymmetric catalysis with chiral ferrocenylphosphine ligands, in Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science (Eds.: A. Togni, T. Hayashi), chapter 2, pp. 105, VCH: Weinheim, 1995.
51. S.-L. You, X.-L. Hou, L.-X. Dai, J. Organomet. Chem. 2001, 637-639, 762;
52. S.-L. You, X.-L. Hou, L.-X. Dai, X.-Z. Zhu, Org. Lett. 2001, 3, 149;
53. J. M. Longmire, B. Wang, X. Zhang, J. Am. Chem. Soc. 2002, 124, 13400.
54. The approaches used to date are the amidation reaction between carboxy-terminated dendrimers with chiral ferrocene diphosphanesequippedwith amineanchoringgroups: a) C. Köllner, B. Pugin, A. Togni, J. Am. Chem. Soc. 1997, 120, 10274;
55. R. Schneider, C. Köllner, I. Weber, A. Togni, Chem. Commun. 1999, 2415;
56. C. Kölner, A. Togni, Can. J. Chem. 2001, 79, 1762;
57. 2 group of a dendrimer: d) L. Routaboul, S. Vincendeau, C.-O. Turrin, A.-M. Caminade, J.-P. Majoral, J.-C. Daran, E. Manoury, J. Organomet. Chem. 2007, 692, 1064.
58. H.-B. Kraatz, J. Inorg. Polym.Mater. 2005, 15, 83.
59. R. Laurent, A.-M. Caminade, J.-P. Majoral, Tetrahedron Lett. 2005, 46, 6503.
60. M. Jasinski, G. Mloston, P. Mucha, A. Linden, H. Heimgartner, Helv. Chim. Acta 2007, 90, 1765.
61. A. J. Lowe, G. A. Dyson, F.M. Pfeffer, Eur. J. Org. Chem. 2008, 1559.
62. J. A. McCubbin, M. L. Maddess, M. Lautens, Org. Lett. 2006, 8, 2993.
63. D. A. Tomalia, J. R. Dewald, US Patent 1985, 4,507,466.
64. T. Hayashi, A. Yamamoto, T. Hagihara, Y. Ito, Tetrahedron Lett. 1986, 27, 191.
65. Z. Otwinowski, W. Minor, HKL Denzo and Scalepack Program Package, Nonius BV, Delft;
66. For a reference, see: b) Z. Otwinowski, W. Minor, Meth. Enzymol. 1997, 276, 307.
67. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
68. G. M. Sheldrick, SHELXL97. Program for Crystal Structure Refinement from Diffraction Data, University of Goettingen: Germany, 1997.
69. A. L. Spek, Platon - a Multipurpose Crystallographic Tool, Utrecht University: Utrecht, 2003, and updates. Available from: http://www.cryst.chem. uu.nl/platon/.