Reversible formation of a planar chiral ferrocenylboroxine and its supramolecular structure

Organometallics

Volumn 30, Issue 24, 2011, Pages 6734-6741

  Thilagar, Pakkirisamy ^a,b   Chen, Jiawei ^a   Lalancette, Roger A ^a   Jäkle, Frieder ^a  

^a RUTGERS UNIVERSITY   (United States)

^b INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2D-NMR SPECTROSCOPY; 4-DIMETHYLAMINOPYRIDINE; BORONIC ACID; BOROXINE RINGS; CATHODIC SHIFTS; FERROCENYL; ISOLATED YIELD; LEWIS BASE; METHOXY SPECIES; NAPHTHYL GROUPS; REDOX PROCESS; REVERSIBLE FORMATION; REVERSIBLE OXIDATION; SINGLE CRYSTAL X-RAY DIFFRACTION; SIX-MEMBERED RINGS; SOLID-STATE STRUCTURES; SUPRAMOLECULAR STRUCTURE;

COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILICA; SILICA GEL; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CYCLIC VOLTAMMETRY;

EID: 84055213551     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200947v     Document Type: Article

References (97)

1. Togni, A., Hayashi, T., Eds. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995.
2. Colacot, T. J. Chem. Rev. 2003, 103, 3101-3118
3. Fu, G. C. Acc. Chem. Res. 2006, 39, 853-860
4. Liu, S.-Y.; Hills, I. D.; Fu, G. C. Organometallics 2002, 21, 4323-4325
5. Liu, S.-Y.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 15352-15353
6. Morgan, I. R.; Di Paolo, A.; Vidovic, D.; Fallis, I. A.; Aldridge, S. Chem. Commun. 2009, 7288-7290
7. Voss, T.; Sortais, J. B.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2011, 30, 584-594
8. Boshra, R.; Doshi, A.; Jäkle, F. Angew. Chem., Int. Ed. 2008, 47, 1134-1137
9. Boshra, R.; Venkatasubbaiah, K.; Doshi, A.; Jäkle, F. Organometallics 2009, 28, 4141-4149
10. Gamboa, J. A.; Sundararaman, A.; Kakalis, L.; Lough, A. J.; Jäkle, F. Organometallics 2002, 21, 4169-4181
11. Boshra, R.; Sundararaman, A.; Zakharov, L. N.; Incarvito, C. D.; Rheingold, A. L.; Jäkle, F. Chem.-Eur. J. 2005, 11, 2810-2824
12. Boshra, R.; Venkatasubbaiah, K.; Doshi, A.; Lalancette, R. A.; Kakalis, L.; Jäkle, F. Inorg. Chem. 2007, 46, 10174-10186
13. Boshra, R.; Doshi, A.; Jäkle, F. Organometallics 2008, 27, 1534-1541
14. Boshra, R.; Doshi, A.; Venkatasubbaiah, K.; Jäkle, F. Inorg. Chim. Acta 2010, 162-166
15. Chen, J.; Venkatasubbaiah, K.; Pakkirisamy, T.; Doshi, A.; Yusupov, A.; Patel, Y.; Lalancette, R. A.; Jäkle, F. Chem.-Eur. J. 2010, 16, 8861-8867
16. Appel, A.; Jäkle, F.; Priermeier, T.; Schmid, R.; Wagner, M. Organometallics 1996, 15, 1188-1194
17. Scheibitz, M.; Bolte, M.; Bats, J. W.; Lerner, H.-W.; Nowik, I.; Herber, R. H.; Krapp, A.; Lein, M.; Holthausen, M.; Wagner, M. Chem.-Eur. J. 2005, 11, 584-603
18. Siebert, W.; Ruf, W.; Schaper, K. J.; Renk, T. J. Organomet. Chem. 1977, 128, 219-224
19. Renk, T.; Ruf, W.; Siebert, W. J. Organomet. Chem. 1976, 120, 1-25
20. Cowan, D. O.; Shu, P.; Hedberg, F. L.; Rossi, M.; Kistenmacher, T. J. J. Am. Chem. Soc. 1979, 101, 1138-1142
21. Wrackmeyer, B.; Dörfler, U.; Milius, W.; Herberhold, M. Polyhedron 1995, 14, 1425-1431
22. Dusemund, C.; Sandanayake, K. R. A. S.; Shinkai, S. Chem. Commun. 1995, 333-334
23. Carpenter, B. E.; Piers, W. E.; McDonald, R. Can. J. Chem. 2001, 79, 291-295
24. Carpenter, B. E.; Piers, W. E.; Parvez, M.; Yap, G. P. A.; Rettig, S. J. Can. J. Chem. 2001, 79, 857-867
25. Scheibitz, M.; Heilmann, J. B.; Winter, R. F.; Bolte, M.; Bats, J. W.; Wagner, M. Dalton Trans. 2005, 159-170
26. Venkatasubbaiah, K.; Zakharov, L. N.; Kassel, W. S.; Rheingold, A. L.; Jäkle, F. Angew. Chem., Int. Ed. 2005, 44, 5428-5433
27. Heilmann, J. B.; Scheibitz, M.; Qin, Y.; Sundararaman, A.; Jäkle, F.; Kretz, T.; Bolte, M.; Lerner, H.-W.; Holthausen, M. C.; Wagner, M. Angew. Chem., Int. Ed. 2006, 45, 920-925
28. Heilmann, J. B.; Qin, Y.; Jäkle, F.; Lerner, H.-W.; Wagner, M. Inorg. Chim. Acta 2006, 359, 4802-4806
29. Venkatasubbaiah, K.; Nowik, I.; Herber, R. H.; Jäkle, F. Chem. Commun. 2007, 2154-2156
30. Kaufmann, L.; Vitze, H.; Bolte, M.; Lerner, H. W.; Wagner, M. Organometallics 2008, 27, 6215-6221
31. Braunschweig, H.; Kaupp, M.; Lambert, C.; Nowak, D.; Radacki, K.; Schinzel, S.; Uttinger, K. Inorg. Chem. 2008, 47, 7456-7458
32. Venkatasubbaiah, K.; Doshi, A.; Nowik, I.; Herber, R. H.; Rheingold, A. L.; Jäkle, F. Chem.-Eur. J. 2008, 14, 444-458
33. Broomsgrove, A. E. J.; Addy, D. A.; Bresner, C.; Fallis, I. A.; Thompson, A. L.; Aldridge, S. Chem.-Eur. J. 2008, 14, 7525-7529
34. Scheibitz, M.; Li, H.; Schnorr, J.; Sánchez Perucha, A.; Bolte, M.; Lerner, H.-W.; Jäkle, F.; Wagner, M. J. Am. Chem. Soc. 2009, 131, 16319-16329
35. Wade, C. R.; Gabbai, F. P. Inorg. Chem. 2010, 49, 714-720
36. Hudson, Z. M.; Wang, S. Acc. Chem. Res. 2009, 42, 1584-1596
37. Morgan, I. R.; Di Paolo, A.; Vidovic, D.; Fallis, I. A.; Aldridge, S. Chem. Commun. 2009, 7288-7290
38. Braunschweig, H.; Breher, F.; Chiu, C.-W.; Gamon, D.; Nied, D.; Radacki, K. Angew. Chem., Int. Ed. 2010, 49, 8975-8978
39. Bagh, B.; Gilroy, J. B.; Staubitz, A.; Müller, J. J. Am. Chem. Soc. 2010, 132, 1794-1795
40. Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527-538
41. Marcelli, T. Angew. Chem., Int. Ed. 2010, 49, 6840-6843
42. Lee, D.; Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 3724-3727
43. Georgiou, I.; Ilyashenko, G.; Whiting, A. Acc. Chem. Res. 2009, 42, 756-768
44. Hall, D. G., Ed. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
45. Kua, J.; Iovine, P. M. J. Phys. Chem. A 2005, 109, 8938-8943
46. Korich, A. L.; Iovine, P. M. Dalton Trans. 2010, 39, 1423-1431
47. Bhat, K. L.; Markham, G. D.; Larkin, J. D.; Bock, C. W. J. Phys. Chem. A 2011, 115, 7785-7793
48. Wu, Q. G.; Wu, G.; Brancaleon, L.; Wang, S. N. Organometallics 1999, 18, 2553-2556
49. Kua, J.; Fletcher, M. N.; Iovine, P. M. J. Phys. Chem. A 2006, 110, 8158-8166
50. Morgan, A. B.; Jurs, J. L.; Tour, J. M. J. Appl. Polym. Sci. 2000, 76, 1257-1268
51. Mehta, M. A.; Fujinami, T.; Inoue, T. J. Power Sources 1999, 82, 724-728
52. Yang, Y.; Inoue, T.; Fujinami, T.; Mehta, M. A. Solid State Ionics 2001, 140, 353-359
53. Yang, Y. S.; Inoue, T.; Fujinami, T.; Mehta, M. A. J. Appl. Polym. Sci. 2002, 84, 17-21
54. Zhou, F.; MacFarlane, D. R.; Forsyth, M. Electrochim. Acta 2003, 48, 1749-1758
55. Nair, N. G.; Blanco, M.; West, W.; Weise, F. C.; Greenbaum, S.; Reddy, V. P. J. Phys. Chem. A 2009, 113, 5918-5926
56. Perttu, E. K.; Arnold, M.; Iovine, P. M. Tetrahedron Lett. 2005, 46, 8753-8756
57. Iovine, P. M.; Fletcher, M. N.; Lin, S. Macromolecules 2006, 39, 6324-6326
58. Qin, Y.; Cui, C.; Jäkle, F. Macromolecules 2007, 40, 1413-1420
59. Tokunaga, Y.; Ito, T.; Sugawara, H.; Nakata, R. Tetrahedron Lett. 2008, 49, 3449-3452
60. Salazar-Mendoza, D.; Guerrero-Alvarez, J.; Höpfl, H. Chem. Commun. 2008, 6543-6545
61. De, P.; Gondi, S. R.; Roy, D.; Sumerlin, B. S. Macromolecules 2009, 42, 5614-5621
62. Korich, A. L.; Walker, A. R.; Hincke, C.; Stevens, C.; Iovine, P. M. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5767-5774
63. Li, Y.; Ding, J.; Day, M.; Tao, Y.; Lu, J.; D'Iorio, M. Chem. Mater. 2003, 15, 4936-4943
64. Alcaraz, G.; Euzenat, L.; Mongin, O.; Katan, C.; Ledoux, I.; Zyss, J.; Blanchard-Desce, M.; Vaultier, M. Chem. Commun. 2003, 2766-2767
65. Kua, J.; Gyselbrecht, C. R. J. Phys. Chem. A 2008, 112, 9128-9133
66. Cote, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166-1170
67. Post, E. W.; Cooks, R. G.; Kotz, J. C. Inorg. Chem. 1970, 9, 1670-1677
68. Bats, J. W.; Ma, K.; Wagner, M. Acta Crystallogr., Sect. C 2002, C58, m129-m132
69. Nowik, I.; Wagner, M.; Herber, R. H. J. Organomet. Chem. 2003, 688, 11-14
70. A similar structure was reported for a thiophenyl-substituted derivative: Hua, D. H.; McGill, J. W.; Robinson, P. D.; Meyers, C. Y. Acta Crystallogr., Sect. E 2001, E57, m413-m415
71. In contrast, in the more extended structure of ferrocenylphenylboroxine, only two ferrocenylphenyl moieties point into the same direction: Makarov, M. V.; Dyadchenko, V. P.; Antipin, M. Y. Russ. Chem. Bull. 2004, 53, 2768-2773
72. Elschenbroich, C.; Wolf, M.; Pebler, J.; Harms, K. Organometallics 2004, 23, 454-459
73. Barrière, F.; Camire, N.; Geiger, W. E.; Mueller-Westerhoff, U. T.; Sanders, R. J. Am. Chem. Soc. 2002, 124, 7262-7263
74. Batsanov, A. S.; Herault, D.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Whiting, A. Organometallics 2007, 26, 2414-2419
75. Arnold, K.; Davies, B.; Herault, D.; Whiting, A. Angew. Chem., Int. Ed. 2008, 47, 2673-2676
76. Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511-3514
77. Pedersen, H. L.; Johannsen, M. J. Org. Chem. 2002, 67, 7982-7994
78. Seitzberg, J. G.; Dissing, C.; Sotofte, I.; Norrby, P.-O.; Johannsen, M. J. Org. Chem. 2005, 70, 8332-8337
79. Venkatasubbaiah, K.; Bats, J. W.; Rheingold, A. L.; Jäkle, F. Organometallics 2005, 24, 6043-6050
80. Venkatasubbaiah, K.; Pakkirisamy, T.; Lalancette, R. A.; Jäkle, F. Dalton Trans. 2008, 4507-4513
81. Venkatasubbaiah, K.; Bolte, M.; Jäkle, F. J. Fluorine Chem. 2010, 131, 1247-1251
82. Beckett, M. A.; Strickland, G. C.; Varma, K. S.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. J. Organomet. Chem. 1997, 535, 33-41
83. Boese, R.; Polk, M.; Blaser, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 245-247
84. Brock, C. P.; Minton, R. P.; Niedenzu, K. Acta Crystallogr. 1987, C43, 1775-1779
85. Avent, A. G.; Lappert, M. F.; Skelton, B.; Raston, C. L.; Engelhardt, L. M.; Harvey, S.; White, A. H. Heteroat. Chem. 1990, 275-285
86. Song, Z. Z.; Zhou, Z. Y.; Mak, T. C. W.; Wong, H. N. C. Angew. Chem., Int. Ed. Engl. 1993, 32, 432-434
87. Satoh, Y.; Cheng, S. Synthesis 1994, 1146-1148
88. Beckett, M. A.; Strickland, G. C.; Varma, K. S.; Hibbs, D. E.; Hursthouse, M. B.; Abdul Malik, K. M. J. Organomet. Chem. 1997, 535, 33-41
89. Haberecht, M. C.; Bolte, M.; Wagner, M.; Lerner, H. W. J. Chem. Crystallogr. 2005, 35, 657-665
90. Bresner, C.; Aldridge, S.; Fallis, I. A.; Ooi, L.-L. Acta Crystallogr., Sect. E 2004, E60, m441-m443
91. Norrild, J. C.; Sotofte, I. J. Chem. Soc., Perkin Trans. 2 2001, 727-732
92. Norrild, J. C.; Sotofte, I. J. Chem. Soc., Perkin Trans. 2 2002, 303-311
93. Zhu, L.; Shabbir, S. H.; Gray, M.; Lynch, V. M.; Sorey, S.; Anslyn, E. V. J. Am. Chem. Soc. 2006, 128, 1222-1232
94. Collins, B. E.; Sorey, S.; Hargrove, A. E.; Shabbir, S. H.; Lynch, V. M.; Anslyn, E. V. J. Org. Chem. 2009, 74, 4055-4060
95. Dickinson, E. J. F.; Limon-Petersen, J. G.; Rees, N. V.; Compton, R. G. J. Phys. Chem. C 2009, 113, 11157-11171
96. Belding, S. R.; Limon-Petersen, J. G.; Dickinson, E. J. F.; Compton, R. G. Angew. Chem., Int. Ed. 2010, 49, 9242-9245
97. The IUPAC-recommended Cahn-Ingold-Prelog (CIP) descriptors p S and p R are used throughout the manuscript to describe the planar chirality; see: Schlögl, K. Top. Stereochem. 1967, 1, 39-91