Preparation, coordination properties and catalytic use of 1′-(diphenylphosphanyl)-1-ferrocenecarboxamides bearing 2-hydroxyethyl pendant groups

Journal of Organometallic Chemistry

Volumn 694, Issue 16, 2009, Pages 2519-2530

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

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Ferrocene; Palladium; Phosphanyl carboxamides; Structure elucidation; Suzuki Miyaura reaction; Water soluble ligands

Indexed keywords

FERROCENE; PHOSPHANYL-CARBOXAMIDES; STRUCTURE ELUCIDATION; SUZUKI-MIYAURA REACTION; WATER-SOLUBLE LIGANDS;

AMIDES; BROMINE COMPOUNDS; CATALYSIS; CATALYSTS; COMPLEXATION; CRYSTAL STRUCTURE; ESTERS; ETHANOL; HYDROGEN; HYDROGEN BONDS; IRON COMPOUNDS; ORGANIC ACIDS; ORGANIC SOLVENTS; PALLADIUM; TOLUENE;

LIGANDS;

EID: 66549091944     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.04.007     Document Type: Article

References (101)

1. In: Štěpnička P. (Ed). Ferrocenes: Ligands. Materials and Biomolecules, Part I - Ferrocene ligands (2008), Wiley, Chichester 3-277 (Chapters 1-7)
2. In: Togni A., and Hayashi T. (Eds). Ferrocenes: Homogeneous Catalysis Organic Synthesis Materials Science. Part I - Homogeneous Catalysis (1995), Wiley-VCH, Weinheim 3-142 (Chapters 1 and 2)
3. Recent reviews: (a). Arrayás R.G., Adrio A., and Carretero J.C. Angew. Chem., Int. Ed. 45 (2006) 7674
4. Atkinson R.C.J., Gibson V.C., and Long N.J. Chem. Soc. Rev. 33 (2004) 313
5. In: Cornils B., and Herrmann W.A. (Eds). Aqueous-phase organometallic catalysis. 2nd ed (2004), Wiley-VCH, Weinheim
6. Joó F. Aqueous Organometallic Catalysis (2002), Kluwer, New York
7. Recent review:. Pinault N., and Bruce D.W. Coord. Chem. Rev. 241 (2003) 1
8. Genet J.P., and Savignac M. J. Organomet. Chem. 576 (1999) 305
9. Pugin B., Groehn V., Moser R., and Blaser H.-U. Tetrahedron: Asymmetry 17 (2006) 544
10. Štěpnička P. Eur. J. Inorg. Chem. (2005) 3787
11. Recent examples: (a). Štěpnička P., and Císařová I. Collect. Czech. Chem. Commun. 71 (2006) 279
12. Lamač M., Císařová I., and Štěpnička P. Eur. J. Inorg. Chem. (2007) 2274
13. Lamač M., Císařová I., and Štěpnička P. Collect. Czech. Chem. Commun. 72 (2007) 985
14. Kühnert J., Lamač M., Rüffer T., Walfort B., Štěpnička P., and Lang H. J. Organomet. Chem. 692 (2007) 4303
15. Bianchini C., Meli A., Oberhauser W., Segarra A.M., Passaglia E., Lamač M., and Štěpnička P. Eur. J. Inorg. Chem. (2008) 441
16. Lamač M., Cvačka J., and Štěpnička P. J. Organomet. Chem. 693 (2008) 3430
17. This was demonstrated for alkali and alkali earth metals salts of Hdpf: (a). Podlaha J., Štěpnička P., Císařová I., and Ludvík J. Organometallics 15 (1996) 543
18. Štěpnička P., and Podlaha J. Inorg. Chem. Commun. 1 (1998) 332
19. Drahoňovský D., Císařová I., Štěpnička P., Dvořáková H., Maloň P., and Dvořák D. Collect. Czech. Chem. Commun. 66 (2001) 588
20. Meca L., Dvořák D., Ludvík J., Císařová I., and Štěpnička P. Organometallics 23 (2004) 2541
21. Kühnert J., Dušek M., Demel J., Lang H., and Štěpnička P. Dalton Trans. (2007) 2802
22. Kühnert J., Císařová I., Lamač M., and Štěpnička P. Dalton Trans. (2008) 2454
23. Štěpnička P., Schulz J., Císařová I., and Fejfarová K. Collect. Czech. Chem. Commun. 72 (2007) 453
24. Kühnert J., Lamač M., Demel J., Nicolai A., Lang H., and Štěpnička P. J. Mol. Catal. A: Chem. 285 (2008) 4
25. Lamač M., Tauchman J., Císařová I., and Štěpnička P. Organometallics 26 (2007) 5042
26. M. Lamač, I. Císařová, P. Štěpnička, New J. Chem. (2009), doi:10.1039/6901262a.
27. See also: W. Zhang, T. Shimanuki, T. Kida, Y. Nakatsuji, I. Ikeda, J. Org. Chem. 64 (1999) 6247.
28. You S.-L., Hou X.-L., Dai L.-X., Dao B.-X., and Sun J. Chem. Commun. (2000) 1933
29. Longmire J.M., Wang B., and Zhang X. Tetrahedron Lett. 41 (2000) 5435
30. You S.-L., Hou X.-L., and -X Dai L. J. Organomet. Chem. 637-639 (2001) 762
31. Longmire J.M., Wang B., and Zhang X. J. Am. Chem. Soc. 124 (2002) 13400
32. Tsukazaki M., Tinkl M., Roglans A., Chapell B.J., Taylor N.J., and Snieckus V. J. Am. Chem. Soc. 118 (1996) 685
33. Laufer R.S., Veith U., Taylor N.J., and Snieckus V. Org. Lett. 2 (2000) 629
34. Metallinos C., Szillat H., Taylor N.J., and Snieckus V. Adv. Synth. Catal. 345 (2003) 370
35. This method is typically used in the preparation of ferrocene conjugates with amino acids and peptides: (a). Kraatz H.-B. J. Inorg. Organomet. Polym. Mater. 15 (2005) 83
36. Metzler-Nolte N., and Salmain M. The bioorganometallic chemistry of ferrocene. In: Štěpnička P. (Ed). Ferrocenes: Ligands, Materials and Biomolecules (2008), Wiley, Chichester 499-639 (Chapter 13)
37. For examples involving phosphanyl-ferrocenecarboxylic acids, see Refs. [7b], [10-12], and [13a].
38. Zhang W., Yoneda Y., Kida T., Nakatsuji Y., and Ikeda I. Tetrahedron: Asymmetry 9 (1998) 3371
39. Štěpnička P., Podlaha J., Gyepes R., and Polášek M. J. Organomet. Chem. 552 (1998) 301
40. Štěpnička P., Císařová I., and Gyepes R. Eur. J. Inorg. Chem. (2006) 926
41. Štěpnička P., and Císařová I. Collect. Czech. Chem. Commun. 71 (2006) 215
42. Coyle R.J., Slovokhotov Y.L., Antipin M.Y., and Grushin V.V. Polyhedron 17 (1998) 3059
43. Gibson V.C., Long N.J., White A.J.P., Williams C.K., Williams D.J., Fontani M., and Zanello P. J. Chem. Soc., Dalton Trans. (2002) 3280
44. Miyaura N. Metal-catalyzed cross-coupling reactions of organoboron compounds with organic halides. In: de Meijere A., and Diederich F. (Eds). Metal-catalyzed Cross-Coupling Reactions vol. 1 (2004), Wiley-VCH, Weinheim 41-123 (Chapter 2)
45. Miayura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
46. Suzuki A. J. Organomet. Chem. 576 (1999) 147
47. Miyaura N. Top. Curr. Chem. 219 (2002) 11
48. Shaughnessy K.H., and DeVasher R.B. Curr. Org. Chem. 9 (2005) 585
49. Li C.-J. Chem. Rev. 105 (2005) 3095
50. Franzén R., and Xu Y. Can. J. Chem. 83 (2005) 266
51. Shaughnessy K.H. Eur. J. Org. Chem. (2006) 1827
52. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
53. Selected examples: (a). Casalnuovo A.L., and Calabrese J.C. J. Am. Chem. Soc. 112 (1990) 4324
54. Genet J.P., Linquist A., Blart E., Mouriès V., Savignas M., and Vaultier M. Tetrahedron Lett. 36 (1995) 1443
55. Dupuis C., Adiey K., Charruault L., Michelet V., Savignac M., and Genet J.P. Tetrahedron Lett. 42 (2001) 6523
56. Moore L.R., and Shaughnessy K.H. Org. Lett. 6 (2004) 225
57. Moore L.R., Western E.C., Craciun R., Spruell J.M., Dixon D.A., O'Halloran K.P., and Shaughnessy K.H. Organometallics 27 (2008) 576
58. Selected examples: (a). Shaughnessy K.H., and Booth R.S. Org. Lett. 3 (2001) 2757
59. DeVasher R.B., Moore L.R., and Shaughnessy K.H. J. Org. Chem. 69 (2004) 7919
60. Hattori H., Fujita K., Muraki T., and Sakaba A. Tetrahedron Lett 48 (2007) 6817
61. Selected references: (a). Nishimura M., Ueda M., and Miyaura N. Tetrahedron 58 (2002) 5779
62. Anderson K.W., and Buchwald S.L. Angew. Chem., Int. Ed. 44 (2005) 6173
63. Konovets A., Penciu A., Framery E., Percina N., Goux-Henry C., and Sinou D. Tetrahedron Lett. 46 (2005) 3205
64. (toluene-ethanol-water + phase transfer catalyst). Paetzold E., and Oehme G. J. Mol. Catal. A: Chem. 152 (2000) 69
65. 2-water). Machnitzki P., Tepper M., Wenz K., Stelzer O., and Herdtweck E. J. Organomet. Chem. 602 (2000) 158
66. (water). Bedford R.B., Blake M.E., Butts C.P., and Holder D. Chem. Commun. (2003) 466
67. (water). Han Y., Huynh V., and Tan G.K. Organometallics 26 (2007) 6581
68. (THF-water). Chang C.-P., Huang Y.-L., and -E Hong F. Tetrahedron 61 (2005) 3835
69. (water and toluene-water). Buchard A., Komly B., Auffrant A., Le Goff X.G., and Le Floch P. Organometallics 27 (2008) 4380
70. (water + phase transfer catalyst). Ma J., Cui X., Gao L., and Wu Y. Inorg. Chem. Commun. 10 (2007) 762
71. (water). Adidou O., Goux-Henry C., Safi M., Soufiaoui M., and Framery E. Tetrahedron Lett. 48 (2008) 7217
72. (water). Bai S.-Q., and Hor T.S.A. Chem. Commun. (2008) 3172
73. King A.O., and Yasuda N. Top. Organomet. Chem. 6 (2004) 205
74. Selected examples (the product is indicated): (a). Wright S.W., Hageman D.L., and McClure L.D. J. Org. Chem. 59 (1994) 6095 (12b)
75. Gala D., Stamford A., Jenkins J., and Kugelman M. Org. Proc. Res. Dev. 1 (1997) 163 (12a)
76. Bumagin N.A., and Bykov V.V. Tetrahedron 53 (1997) 14437 (10a)
77. Alonso D.A., Nájera C., and Pacheco C. J. Org. Chem. 67 (2002) 5588 (12a)
78. Nájera C., Gil-Moltó J., and Karlström S. Adv. Synth. Catal. 346 (2004) 1798 (12a)
79. Tzschucke C.C., and Bannwarth W. Helv. Chim. Acta 87 (2004) 2882 (12a)
80. Baleizão C., Corma A., Tacís H., and Leyva A. J. Org. Chem. 69 (2004) 439
81. Vassylyev O., Chen J., Panarello A.P., and Khinast J.G. Tetrahedron Lett. 46 (2005) 6856 (12a)
82. Lu G., Franzén R., Zhang Q., and Xu Y. Tetrahedron Lett. 46 (2005) 4255 (10a, 12a)
83. Jiang X., Sclafani H., Prasad K., Repič O., and Blacklock T.J. Org. Proc. Res. Develop. 11 (2007) 769 (12a)
84. Chien S.W., and Hor T.S.A. The coordination homogeneous catalytic chemistry of 1,1(-bis(diphenylphosphino)ferrocene and its chalcogenide derivatives. In: Štěpnička P. (Ed). Ferrocenes: Ligands, Materials and Biomolecules (2008), Wiley, Chichester pp. 33-116 (Chapter 2)
85. Gan K.-S., and Hor T.S.A. 1,1(-Bis(diphenylphosphino)ferrocene - coordination chemistry, organic syntheses, and catalysis. In: Togni A., and Hayashi T. (Eds). Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science (1995), VCH, Weinheim 3-104 (Chapter 1)
86. Colacot T.J., and Parisel S. Synthesis coordination chemistry and catalytic use of dppf analogs. In: Štěpnička P. (Ed). Ferrocenes: Ligands, Materials and Biomolecules (2008), Wiley, Chichester 117-140 (Chapter 3)
87. Jiang N., and Ragauskas A.J. Tetrahedron Lett. 47 (2006) 197
88. Braga D., Curzi M., Giaffreda S.L., Grepioni F., Maini L., Petersen A., and Polito M. Crystal engineering with ferrocene compounds. In: Štěpnička P. (Ed). Ferrocenes: Ligands, Materials and Biomolecules (2008), Wiley, Chichester 465-498 (Chapter 12)
89. Braga D. Chem. Commun. (2003) 2751
90. Braga D., Grepioni F., and Desiraju G.R. Chem. Rev. 98 (1998) 1375
91. Drew D., and Doyle J.R. Inorg. Synth. 13 (1972) 47
92. Mikroyannidis J.A., and Spiliopoulos I.K. Polym. Sci., Part A: Polym. Chem. 42 (2004) 1768
93. Sakai N., Moriya T., and Konakahara T. J. Org. Chem. 72 (2007) 5920
94. Karitzky A.R., Toader D., and Xie L. Synthesis (1996) 1425
95. Zhao J., and Larock R.C. J. Org. Chem. 72 (2007) 583
96. Costa A., Nájera C., and Sansano J.M. J. Org. Chem. 67 (2002) 5216
97. Crosignani S., Gonzales J., and Swinnen D. Org. Lett. 6 (2004) 4579
98. Z. Otwinowski, W. Minor, hkl denzo and scalepack Program Package, Nonius BV, Delft, The Netherlands. For a reference, see: Z. Otwinowski, W. Minor, Meth. Enzymol. 276 (1997) 307.
99. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115
100. Sheldrick G.M. shelxl97. Program for Crystal Structure Refinement from Diffraction Data (1997), University of Goettingen, Germany
101. A. L. Spek, Platon-a multipurpose crystallographic tool, Utrecht University, Utrecht, The Netherlands, 2003 and updates. http://www.cryst.chem.uu.nl/platon/. For a reference, see: A. L. Spek, J. Appl. Cryst. 36 (2003) 7.