Synthesis, coordination properties, and catalytic use of phosphinoferrocene carboxamides bearing donor-functionalized amide substituents

Organometallics

Volumn 32, Issue 20, 2013, Pages 5754-5765

  Štěpnička, Petr ^a   Schneiderová, Barbora ^a   Schulz, Jiří ^a   Císařová, Ivana ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE COUPLINGS; CATALYTIC PERFORMANCE; COORDINATION BEHAVIOR; COORDINATION PROPERTIES; COUPLING PRODUCT; MODEL SUBSTRATES; PHENYLBORONIC ACIDS; SUZUKI-MIYAURA CROSS-COUPLING;

CHEMICAL REACTIONS; LIGANDS; ORGANOMETALLICS; PALLADIUM COMPOUNDS;

AMIDES;

EID: 84887095191     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400282z     Document Type: Article

References (95)

1. Štěpnička, P. Chem. Soc. Rev. 2012, 41, 4273
2. You, S.-L.; Hou, X.-L.; Dai, L.-X.; Cao, B.-X.; Sun, J. Chem. Commun. 2000, 1933
3. Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435
4. You, S.-L.; Hou, X.-L.; Dai, L.-X.; Zhu, X.-Z. Org. Lett. 2001, 3, 149
5. You, S.-L.; Hou, X.-L.; Dai, L.-X. J. Organomet. Chem. 2001, 637-639, 762
6. You, S.-L.; Luo, Y.-M.; Deng, W.-P.; Hou, X.-L.; Dai, L.-X. J. Organomet. Chem. 2001, 637-639, 845
7. Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400
8. Lamač, M.; Tauchman, J.; Dietrich, S.; Císař ová, I.; Lang, H.; Štěpnička, P. Appl. Organomet. Chem. 2010, 24, 326
9. Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247
10. Zhang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371
11. Deng, W.-P.; You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508
12. Drahoňovský, D.; Císařová, I.; Štěpnička, P.; Dvořáková, H.; Maloň, P.; Dvořák, D. Collect. Czech. Chem. Commun. 2001, 66, 588
13. El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111, 6557
14. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606, and references therein.
15. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685
16. Jendralla, H.; Paulus, E. Synlett 1997, 471
17. Laufer, R. S.; Veith, U.; Taylor, N. J.; Snieckus, V. Org. Lett. 2000, 2, 629
18. Metallinos, C.; Szillat, H.; Taylor, N. J.; Snieckus, V. Adv. Synth. Catal. 2003, 345, 370
19. Stavrakov, G.; Philipova, I.; Ivanova, B.; Dimitrov, V. Tetrahedron: Asymmetry 2010, 21, 1845
20. Philipova, I.; Stavrakov, G.; Chimov, A.; Nikolova, R.; Shivachev, B.; Dimitrov, V. Tetrahedron: Asymmetry 2011, 22, 970
21. Štěpnička, P.; Solařová, H.; Lamač, M.; Císařová, I. J. Organomet. Chem. 2010, 695, 2423
22. Podlaha, J.; Štěpnička, P.; Císař ová, I.; Ludvík, J. Organometallics 1996, 15, 543
23. Štěpnička, P. Eur. J. Inorg. Chem. 2005, 3787
24. Hdpf-amides represent an entry among functional analogues of the ubiquitous 1,1′-bis(diphenylphoshino)ferrocene: Ště pnička, P. 1′-Functionalised Ferrocene Phosphines: Synthesis, Coordination Chemistry and Catalytic Applications. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; Wiley: Chichester, 2008;, Chapter 5, p 177.
25. Meca, L.; Dvořák, D.; Ludvík, J.; Císařová, I.; Štěpnička, P. Organometallics 2004, 23, 2541
26. Slone, C. S.; Weinberger, D. A.; Mirkin, C. A. Prog. Inorg. Chem. 1999, 48, 233
27. Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27
28. Ferrocenes: Ligands, Materials and Biomolecules; Ště pnička, P., Ed.; Wiley: Chichester, 2008.
29. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A.; Hayashi, T., Eds.; Wiley-VCH: Weinheim, 1995.
30. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J. Chem. Soc. Rev. 2004, 33, 313
31. Barbaro, P.; Bianchini, C.; Giambastiani, G.; Parisel, S. L. Coord. Chem. Rev. 2004, 248, 2131
32. Goméz Arrayás, R.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674
33. Kühnert, J.; Lamač, M.; Demel, J.; Nicolai, A.; Lang, H.; Štěpnička, P. J. Mol. Catal. A: Chem. 2008, 285, 41
34. Lamač, M.; Tauchman, J.; Císařová, I.; Štěpnička, P. Organometallics 2007, 26, 5042
35. Schulz, J.; Císařová, I.; Ště pnička, P. J. Organomet. Chem. 2009, 694, 2519
36. Tauchman, J.; Císařová, I.; Ště pnička, P. Organometallics 2009, 28, 3288
37. Tauchman, J.; Císařová, I.; Ště pnička, P. Eur. J. Org. Chem. 2010, 4276
38. Tauchman, J.; Císařová, I.; Ště pnička, P. Dalton Trans. 2011, 40, 11748
39. Schulz, J.; Císařová, I.; Ště pnička, P. Organometallics 2012, 31, 729
40. Tauchman, J.; Therrien, B.; Süss-Fink, G.; Ště pnička, P. Organometallics 2012, 31, 3985
41. Schulz, J.; Císařová, I.; Ště pnička, P. Eur. J. Inorg. Chem. 2012, 5000
42. Tauchman, J.; Süss-Fink, G.; Štěpnička, P.; Zava, O.; Dyson, P. J. J. Organomet. Chem. 2013, 723, 233
43. Kühnert, J.; Dušek, M.; Demel, J.; Lang, H.; Štěpnička, P. Dalton Trans. 2007, 2802
44. Kühnert, J.; Císařová, I.; Lamač, M.; Štěpnička, P. Dalton Trans. 2008, 2454
45. Štěpnička, P.; Krupa, M.; Lamač, M.; Císařová, I. J. Organomet. Chem. 2009, 694, 2987
46. Feng, X.; Pugin, B.; Kusters, E.; Sedelmeier, G.; Blaser, H.-U. Adv. Synth. Catal. 2007, 349, 1803 (amides from carboxylated Josiphos)
47. p)-2-[1-(diphenylphosphino)ethyl]ferrocenecarboxylic acid)
48. Lamač, M.; Císařová, I.; Ště pnička, P. New J. Chem. 2009, 33, 1549 (amides from planar-chiral, monocarboxylated 1,1′-bis(diphenylphosphino)ferrocene). See also refs 2 and 4
49. Freixa, Z.; Leeuwen, P. W. N. M. Coord. Chem. Rev. 2008, 252, 1755
50. Bessel, C. A.; Aggarwal, P.; Marschilok, A. C.; Takeuchi, K. J. Chem. Rev. 2001, 101, 1031
51. Haaland, A. Acc. Chem. Res. 1979, 12, 415
52. Gardner, A. B.; Howard, J.; Waddington, T. C.; Richardson, R. M.; Tomkinson, J. Chem. Phys. 1981, 57, 453
53. Pinault, N.; Bruce, D. W. Coord. Chem. Rev. 2003, 241, 1
54. Shaughnessy, K. H. Chem. Rev. 2009, 109, 643
55. Aqueous-Phase Organometallic Catalysis, 2 nd ed.; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 2004.
56. Smith, R. T.; Baird, M. C. Transition Met. Chem. 1981, 6, 197
57. Smith, R. T.; Baird, M. C. Inorg. Chim. Acta 1982, 62, 135
58. Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138
59. Peiffer, G.; Chhan, S.; Bendayan, A.; Waegell, B.; Zahra, J.-P. J. Mol. Catal. 1990, 59, 1
60. Bitterer, F.; Kucken, S.; Stelzer, O. Chem. Ber. 1995, 128, 275
61. Hessler, A.; Kucken, S.; Stelzer, O.; Blotevogel-Baltronat, J.; Sheldrick, W. S. J. Organomet. Chem. 1995, 501, 293
62. Papagni, A.; Trombini, C.; Lombardo, M.; Bergantin, S.; Chams, A.; Chiarucci, M.; Miozzo, L.; Parravicini, M. Organometallics 2011, 30, 4325
63. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1
64. Hartley, F. R. The Chemistry of Platinum and Palladium; Applied Science: London, 1973.
65. Butler, I. R.; Kalaji, M.; Nehrlich, L.; Hursthouse, M.; Karaulov, A. I.; Malik, K. M. A. Chem. Commun. 1995, 459
66. Hildebrandt, A.; Wetzold, N.; Ecorchard, P.; Walfort, B.; Rüffer, T.; Lang, H. Eur. J. Inorg. Chem. 2010, 3615
67. Van Der Steen, F. H.; Kanters, J. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1986, 42, 547
68. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745
69. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937
70. Mernyi, A.; Kratky, C.; Weissensteiner, W.; Widhalm, M. J. Organomet. Chem. 1996, 508, 209
71. Woo, T. K.; Pioda, G.; Rothlisberger, U.; Togni, A. Organometallics 2000, 19, 2144
72. Liptau, P.; Seki, T.; Kehr, G.; Abele, A.; Fröhlich, R.; Erker, G.; Grimme, S. Organometallics 2003, 22, 2226
73. Metallinos, C.; Zaifman, J.; Van Belle, L.; Dodge, L.; Pilkington, M. Organometallics 2009, 28, 4534
74. Štěpnička, P.; Schulz, J.; Klemann, T.; Siemeling, U.; Císařová, I. Organometallics 2010, 29, 3187
75. Schuecker, R.; Zirakzadeh, A.; Mereiter, K.; Spindler, F.; Weissensteiner, W. Organometallics 2011, 30, 4711
76. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158
77. Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003, 22, 4490
78. Hagopian, L. E.; Campbell, A. N.; Golen, J. A.; Rheingold, A. L.; Nataro, C. J. Organomet. Chem. 2006, 691, 4890
79. Cortes, J. G. L.; Ramon, O.; Vincendeau, S.; Serra, D.; Lamy, F.; Daran, J.-C.; Manoury, E.; Gouygou, M. Eur. J. Inorg. Chem. 2006, 5148
80. Wang, Y.; Weissensteiner, W.; Spindler, F.; Arion, V. B.; Mereiter, K. Organometallics 2007, 26, 3530
81. Wang, Y.; Sturm, T.; Steurer, M.; Arion, V. B.; Mereiter, K.; Spindler, F.; Weissensteiner, W. Organometallics 2008, 27, 1119
82. Buergler, J. F.; Togni, A. Organometallics 2011, 30, 4742
83. Štěpnička, P.; Císařová, I.; Schulz, J. Organometallics 2011, 30, 4393 and ref 24f
84. 13C NMR of Transition Metal Phosphane Complexes. In NMR Basic Principles and Progress; Diehl, P.; Fluck, E.; Kosfeld, R., Eds.; Springer: Berlin, 1979; Vol. 16, Chapter E, p 65, and references therein.
85. Tani, K.; Yabuta, M.; Nakamura, S.; Yamagata, T. J. Chem. Soc., Dalton Trans. 1993, 2781
86. Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, Vol. 1, Chapter 2, p 41.
87. Miayura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
88. Suzuki, A. J. Organomet. Chem. 1999, 576, 147
89. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
90. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725
91. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302
92. Štěpnička, P.; Schulz, J.; Císař ová, I.; Fejfarová, K. Collect. Czech. Chem. Commun. 2007, 72, 453
93. Sheldrick, G. M. Acta Crystallogr. A, Fundam. Crystallogr. 2008, 64, 112
94. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115
95. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7