Aromatic borataheterocycles: Surrogates for cyclopentadienyl in transition-metal complexes

Organometallics

Volumn 28, Issue 15, 2009, Pages 4236-4248

  Ashe III, Arthur J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION CHEMISTRY; CYCLOPENTADIENYLS; FIVE-MEMBERED RINGS; ISOELECTRONIC SUBSTITUTION; ORGANOMETALLIC COMPOUNDS; SIX-MEMBERED RINGS; TRANSITION-METAL COMPLEX;

DYES; METAL COMPLEXES; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); THIOPHENE; TRANSITION METALS;

COORDINATION REACTIONS;

EID: 68149161075     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900308e     Document Type: Review

References (94)

1. Herberich, G. E.; Ohst, H. Adv. Organomet. Chem. 1986, 25,199.
2. Ashe, A. J., III; Al-Ahmad, S.; Fang, X. G. J. Organomet. Chem. 1999, 581, 92.
3. Fu, G. C. Adv. Organomet. Chem. 2001, 47, 101.
4. Norris, P. In Comprehensive Heterocyclic Chemistry III; Black, D. StC, Ed.; Elsevier: Oxford, U.K. 2008; Vol. 7, p 1049.
5. Herberich, G. E.; Greiss, G.; Heil, H. F. Angew. Chem., Int. Ed. Engl. 1970, 9, 805.
6. Herberich, G. E.; Becker, H. J.; Carsten, K.; Engelke, C.; Koch, W. Chem. Ber. 1976, 109, 3382.
7. Ashe, A. J., III; Shu, P. J. Am. Chem. Soc. 1971, 93, 1804.
8. (a) Ashe, A. J., III; Meyers, E.; Shu, P.; Von Lehman, T. M.; Bastide, J. J. Am. Chem. Soc. 1975, 97, 6865.
9. (b) Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Müller, C. J. Am. Chem. Soc. 1996, 118, 2291.
10. (c) Ashe, A. J., III; Kampf, J. W.; Müller, C.; Schneider, M. Organometallics 1996, 15, 387.
11. 2 for b, Ph for c, and vinyl for d.
12. Huttner, G.; Kreig, B.; Gartzke, W. Chem. Ber. 1972, 105, 3424.
13. Bazan, G. C.; Rodriguez, G.; Ashe, A. J., III; Al-Ahmad, S.; Kampf, J. W. Organometallics 1997, 16, 2492.
14. Elschenbroich, C. In Organometallics, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2005; p 560.
15. Ashe, A. J., III. In Comprehensive Heterocyclic Chemistry III; Joule, J., Ed.; Elsevier: Oxford, U.K. 2008; Vol. 4, p 1189.
16. Varvounis, G. In Comprehensive Heterocyclic Chemistry III; Joule, J., Ed.; Elsevier: Oxford, U.K. 2008; Vol. 4, p 1225.
17. Ashe, A. J., III; Fang, X. G.; Kampf, J. W. Organometallics 1998, 17, 2379.
18. Ashe, A. J., III; Kampf, J. W.; Schiesher, M. W. Organometallics 2000, 79, 4681.
19. Ashe, A. J., III; Fang,X. G.; Kampf, J. W. Organometallics 1999, 18, 1821.
20. Brandsma, L.; Verkruijsse, H. D. In Synthesis of Acetylenes, Alienes, and Cumulenes; Elsevier: Amsterdam, 1981; p 73.
21. Ashe, A. J., III; Fang,X. D.; Kampf, J. W. Organometallics 2000, 19,4935.
22. For CpLi see: Cox, R. H.; Terry, H. W., Jr. J Magn. Reson. 1974, 14, 317.
23. (a) Olah, G. A.; Asensio, G.; Mayr, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1978, 100, 4347.
24. (b) Jutzi, P.; Meyer, M.; Rasika Dias, H. V.; Power, P. P. J. Am. Chem. Soc. 1990, 112, 4841.
25. Wrackmeyer, B. Annu. Rep. NMR Spectrosc. 1988, 20, 1.
26. Elschenbroich, C.; Salzer, A. In Organometallics, 2nd ed.; VCH: Weinheim, Germany, 1991; pp 296, 307.
27. Wiberg, E. Naturwissenschaften 1948, 35, 182.
28. (a) Greenwood, N. N.; Thomas, B. S. In Comprehensive Inorganic Chemistry; Bailor, J. C., Emeléus, H. J., Nyholm, R., Trotman-Dickenson, A. F., Eds.; Pergamon: Oxford, U.K., 1973; Vol. 1, p 916.
29. (b) Pelter, A; Smith, K. In Comprehensive Organic Chemistry; Barton, D., Ollis, W D., Eds.; Pergamon: Oxford, U.K., 1979; Vol. 3, p 925.
30. (a) Dill, J. D.; Schleyer, P. v. R.; Pople, J. A. J. Am. Chem. Soc. 1975,97,3402.
31. (b) Budzelaar, P. H. M.; Kos, A. J.; Clark, T.; Schleyer, P. v. R. Organometallics 1985, 4,429.
32. (a) Imbery, D.; Jaeschke, A.; Friebolin, H. Org. Magn. Reson. 1970, 2, 271.
33. (b) Freibolin, H.; Rensch, R.; Wendel, H. Org. Magn. Reson. 1976, 8, 287.
34. (c) Freibolin, H. Basic One- and Two-Dimensional NMR Spectroscopy, 3rd ed.; Wiley-VCH: Weinheim, Germany, 1998; p 316.
35. Bajgur,C.S.;Tikkanen,W. R.;Petersen, J.L.Inorg. Chem. 1985, 24, 2539.
36. Schiesher, M. W. Ph.D. Dissertation; University of Michigan, 2002;
37. Chem. Abstr. 2002, 139, 22313.
38. Chen, J.; Fang, X. D.; Bajko, Z.; Kampf, J. W.; Ashe, A.J., III. Organometallics 2004, 23, 5088.
39. Bajko, Z.; Kampf, J. W.; Ashe, A. J., III. Private communication to the Cambridge Crystallographic Database, deposition number CCDC 732430.
40. Ashe, A. J., III; Bajko, Z.; Fang, X. D.; Kampf, J. W.; Yang, H. Phosphorus, Sulfur, Silicon Relat. Elem. 2004,179, 711.
41. Massol, M; Satgé, J.; Bouyssières, B. Synth. Inorg. Met.-Org. Chem. 1973, 3, 1.
42. Chaudret, B.; Jalon, F. A. J. Chem. Soc, Chem. Commun. 1988, 711.
43. Herberich, G. E.; Becker, H. J. Angew. Chem. Int. Ed., Engl. 1973, 12, 764.
44. (a) Schmid, G. In Comprehensive Heterocyclic Chemistry II; Shinkai, I., Ed.; Pergamon: Oxford, U.K., 1996; Vol. 3, p 739.
45. (b) Schmid, G. Comments Inorg. Chem. 1985, 4, 17.
46. Bosdet, M. J. D.; Piers, W. E. Can. J. Chem. 2009, 87, 8.
47. Hänssgen, D.; Odenhausen, E. Chem. Ber. 1979, 112, 2389.
48. Schulze, J.; Schmid, G. J. Organomet. Chem. 1980, 193, 83.
49. Liu, S.-Y.; Lo, M. M.-C; Fu, G. C Angew. Chem., Int. Ed. 2002, 41, 174.
50. Liu, S.-Y.; Hills, I. D.; Fu, G. C Organometallics 2002, 21, 4323.
51. 5Cp: Manriquez, J. M.; Fagan, P. J.; Schertz, L. D., Marks, T. J. Inorg. Synth. 1990, 28, 317 and references cited therein,
52. 4Cp: Chirik, P. J. Dalton Trans. 2007, 16.
53. Fang, X. D.; Assoud, J. Organometallics 2008, 27, 2408.
54. Ashe, A. J., III.; Fang, X.-D. Org. Lett. 2000, 2, 2089.
55. Yang, H.; Fang, X. D.; Kampf, J. W.; Ashe, A. J., III. Polyhedron 2005, 24, 1280.
56. Ashe, A. J., III; Yang, H.; Fang, X. D.; Kampf, J. W. Organometallics 2002, 21, 4578.
57. Fang, X. D.; Yang, H.; Kampf, J. W.; Banaszak Holl, M. M.; Ashe, A. J., III. Organometallics 2006, 25, 513.
58. Nagy, S.; Krishnamatti, R.; Etherton, B. P. U.S. Patent 6,228,959, 2001;
59. Chem. Abstr. 1997, 126, 19432J.
60. Wang, Q.; Zoricak, P.; Gao, X. Can. Pat. Appl. 2,225,014,1999;
61. Chem. Abstr. 1999, 142, 219701.
62. Ashe, A. J., III; Yang, H.; Timmers, F. J. U.S. Patent 7074865 B2, 2006;
63. Chem. Abstr. 2003, 139, 323949.
64. Gladysz, J. A., Ed. Chem. Rev. 2000, 100, 1167-1682.
65. Fang, X. D.; Deng, Y.; Xie, Q.; Moingeon, F. Organometallics 2008 27 2892
66. Liu, S.-Y.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 15352.
67. Liu, S.-Y; Lo, M. M.-C.; Fu, G. C. Tetrahedron 2006,62,11343.
68. Reviews: (a) Dewar, M. J. S. Prog. Boron Chem. 1964, 1, 235.
69. (b) Fritsch, A. J. Chem. Heterocycl. Compd. 1977, 30, 381.
70. Dewar, M. J. S.; Dietz, R. J. Chem. Soc. 1959, 2728.
71. Paetzold, P.; Stanescu, C.; Stubenrauch, J. R.; Bienmüller, M.; Englert, U. Z. Anorg. Allg. Chem. 2004, 630,2632.
72. Pan, J.; Kampf, J. W.; Ashe, A. J., III. Organometallics 2009, 28, 506.
73. Pan, J.; Kampf, J. W.; Ashe, A. J., III. Organometallics 2004, 23, 5626.
74. Ashe, A. J., III; Fang, X. D.; Fang, X. G.; Kampf, J. W. Organometallics 2001, 20, 5413.
75. Pan, J.; Kampf, J. W. Organometallics 2008, 27, 1345.
76. Bynum, R. V.; Hunter, W. E.; Rogers, R. D.; Atwood, J. L. Inorg. Chem. 1980, 19, 2368.
77. Garrett, C. E.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 7479.
78. Pan, J.; Kampf, J. W.; Ashe, A. J., III. J. Orgmet. Chem. 2009, 694, 1036.
79. Bordwell, F. G. Ace. Chem. Res. 1988, 21,456.
80. Sammakia, T.; Hurley, T. B. J. Org. Chem. 1999, 64, 4652.
81. For reviews, see: (a) Dötz, K. H.; Wenzel, B.; Jahr, H. C. Top. Curr. Chem. 2004, 248, 63.
82. (b) Dötz, K. H.; Jahr, H. C. Chem. Reel. 2004, 4, 61.
83. (c) Oprunenko, Y. F. Russ. Chem. Rev. 2000, 69, 683.
84. (d) Morris, M. J. In Comprehensive Organometallic Chemistry II; Abel, E. W, Stone, F. G. A.,Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 5, p 501.
85. Ceccon, A.; Gambaro, A.; Gottardi, F.; Santi, S.; Venzo, A.; Lucchini, V. J. Organomet. Chem. 1989, 379, 67.
86. Ceccon, A.; Gambaro, A.; Gottardi, F.; Santi, S. J.; Venzo, A. J. Organomet. Chem. 1991, 412, 85.
87. However, see: Zhu, G.; Tanski, J. M.; Churchill, D. G.; Janak, K. E.; Parkin, G. J. Am. Chem. Soc. 2002, 124, 13658.
88. Pan, J.; Kampf, J. W.; Ashe, A. J., III. Organometallics 2006,25, 197.
89. Pan, J.; Wang, J.; Banaszak Holl, M. M.; Kampf, J. W.; Ashe, A. J., III. Organometallics 2006, 25, 3463.
90. (a) Marwitz, A. J. V.; Hatus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 973.
91. (b) Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2008, 130, 7250.
92. (c) Marwitz, A. J. V; Abbey, E. R.; Jenkins, J. T.; Zakharov, L. V.; Liu, S.-Y. Org. Lett. 2007, 9, 4905.
93. Pan, J.; Kampf, J. W.; Ashe, A. J., III. Org. Lett. 2007, 9, 679.
94. Liu, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2008, 47, 242 and references cited therein.