Synthesis, structural characterization, and preliminary reactivity profile of a series of monocyclopentadienyl, monoacetamidinate titanium(III) alkyl complexes bearing β-hydrogens

Organometallics

Volumn 29, Issue 23, 2010, Pages 6587-6593

  Trunkely, Emily F ^a   Epshteyn, Albert ^a   Zavalij, Peter Y ^a   Sita, Lawrence R ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGOSTIC INTERACTIONS; ALKYL COMPLEXES; ALKYL GROUPS; ALKYL LITHIUM REAGENTS; CARBON BOND; DIETHYL ETHERS; HIGH YIELD; ISOCYANIDES; METAL CENTERS; SINGLE CRYSTAL X-RAY ANALYSIS; SOLID-STATE STRUCTURES; STRUCTURAL CHARACTERIZATION; THERMALLY STABLE;

ALKYLATION; COMPLEXATION; CRYSTALLINE MATERIALS; CYANIDES; ETHERS; HYDROGEN; PARAMAGNETIC MATERIALS; PARAMAGNETISM; TITANIUM; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAYS;

TITANIUM COMPOUNDS;

EID: 78649816966     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100877d     Document Type: Article

References (91)

1. For general discussions and applications of group 4 organometallic chemistry, see: Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
2. Marek, I., Ed. Titanium and Zirconium in Organic Synthesis; Wiley-VCH: New York, 2002.
3. For investigations of Ti(II) and Zr(II) chemistry, see, for instance: Cohen, S. A.; Auburn, P. R.; Bercaw, J. E. J. Am. Chem. Soc. 1983, 105, 1136-1143
4. Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058
5. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130
6. Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641
7. Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111-9119
8. Negishi, E. Dalton Trans. 2005, 827-848
9. Huynh, K.; Vignolle, J.; Tilley, T. D. Angew. Chem., Int. Ed. 2009, 48, 2835-2837
10. Miller, A. D.; Tannaci, J. F.; Johnson, S. A.; Hyuk, L.; McBee, J. L.; Tilley, T. D. J. Am. Chem. Soc. 2009, 131, 4917-4927, and references therein.
11. 1,) oxidation state is required for the (stereoselective) coordination polymerization of styrene; see, for instance: Brintzinger, H. H.; Fischer, D.; Mulhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170
12. Guram, A. S.; Jordan, R. F. Compr. Organomet. Chem. 1995, 4, 589-625
13. McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587-2598
14. Tomotsu, N.; Ishihara, N.; Newman, T. H.; Malanga, M. T. J. Mol. Catal. A: Chem. 1998, 128, 167-190
15. Pellecchia, C.; Grassi, A. Top. Catal. 1999, 7, 125-132
16. Rodrigues, A. S.; Kirillov, E.; Carpentier, J. F. Coord. Chem. Rev. 2008, 252, 2115-2136
17. Nifant'ev, I. E.; Ustynyuk, L. Y.; Besedin, D. V. Organometallics 2003, 22, 2619-2629
18. Pastorino, R.; Capacchione, C.; Ferro, R.; Milione, S.; Grassi, A. Macromolecules 2009, 42, 2480-2487
19. Mahanthappa, M. K.; Waymouth, R. M. J. Am. Chem. Soc. 2001, 123, 12093-12094
20. Michiue, K.; Jordan, R. F. Macromolecules 2003, 36, 9707-9709
21. Pattiasina, J. W.; Hissink, C. E.; de Boer, J. L.; Meetsma, A.; Teuben, J. H.; Spek, A. L. J. Am. Chem. Soc. 1985, 107, 7758-7759
22. Luinstra, G. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1990, 1470-1471
23. Luinstra, G. A.; Ten Cate, L. C.; Heeres, H. J.; Pattiasina, J. W.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3227-3237
24. Luinstra, G. A.; Teuben, J. H. J. Organomet. Chem. 1991, 420, 337-344
25. Luinstra, G. A.; Vogelzang, J.; Teuben, J. H. Organometallics 1992, 11, 2273-2281
26. 3]; X = Cl, Me)
27. Bailey, B. C.; Basuli, F.; Huffman, J. C.; Mindiola, D. J. Organometallics 2006, 25, 3963-3968
28. Bai, G.; Wei, P.; Stephan, D. W. Organometallics 2006, 25, 2649-2655
29. For CpAm group 4 Zr(II), Zr(IV), and Hf(IV) β-hydrogen-bearing alkyl complexes, see: Keaton, R. J.; Koterwas, L. A.; Fettinger, J. C.; Sita, L. R. J. Am. Chem. Soc. 2002, 124, 5932-5933
30. Keaton, R. J.; Sita, L. R. Organometallics 2002, 21, 4315-4317
31. Keaton, R. J.; Sita, L. R. Organometallics 2002, 21, 4315-4317
32. Zhang, Y.; Keaton, R. J.; Sita, L. R. J. Am. Chem. Soc. 2003, 125, 8749-8747
33. Kissounko, D. A.; Epshteyn, A.; Fettinger, J. C.; Sita, L. R. Organometallics 2006, 25, 1076-1078
34. Harney, M. B.; Keaton, R. J.; Fettinger, J. C.; Sita, L. R. J. Am. Chem. Soc. 2006, 128, 3420-3432
35. Fontaine, P. P.; Epshteyn, A.; Zavalij, P. Y.; Sita, L. R. J. Organomet. Chem. 2007, 692, 4683-4689
36. Epshteyn, A.; Trunkely, E. F.; Kissounko, D. A.; Fettinger, J. C.; Sita, L R. Organometallics 2009, 28, 2520-2526
37. 0) β-hydrogen-bearing alkyl complexes, see: Epshteyn, A.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2006, 128, 16052-16053
38. For cationic CpAm Zr(IV) and Hf(IV) β-hydrogen-bearing alkyl complexes that are active for the living (stereoselective) coordination polymerization of ethene, propene, α-olefins, and α,ω- nonconjugated dienes, see: Jayaratne, K. C.; Sita, L. R. J. Am. Chem. Soc. 2000, 122, 958-959
39. Jayaratne, K. C.; Sita, L. R. J. Am. Chem. Soc. 2001, 123, 10754-10755
40. Keaton, R. J.; Jayaratne, K. C.; Henningsen, D. A.; Koterwas, L. A.; Sita, L. R. J. Am. Chem. Soc. 2001, 123, 6197-6198
41. Keaton, R. J.; Sita, L. R. J. Am. Chem. Soc. 2002, 124, 9070-9071
42. Zhang, Y.; Keaton, R. J.; Sita, L. R. J. Am. Chem. Soc. 2003, 125, 9062-9069
43. Harney, M. B.; Keaton, R. J.; Sita, L. R. J. Am. Chem. Soc. 2004, 126, 4536-4537
44. Zhang, Y.; Reeder, E. K.; Keaton, R. J.; Sita, L. R. Organometallics 2004, 23, 3512-3520
45. Kissounko, D. A.; Zhang, Y.; Harney, M. B. Adv. Synth. Catal. 2005, 347, 426-432
46. Harney, M. B.; Zhang, Y.; Sita, L. R. Angew. Chem., Int. Ed. 2006, 45, 2400-2404
47. Harney, M. B.; Zhang, Y.; Sita, L. R. Angew. Chem., Int. Ed. 2006, 45, 6140-6144
48. Zhang, W.; Sita, L. R. J. Am. Chem. Soc. 2008, 130, 442-443
49. Zhang, W.; Sita, L. R. Adv. Synth. Catal. 2008, 350, 439-447
50. Zhang, W.; Wei, J.; Sita, L. R. Macromolecules 2008, 41, 7829-7833
51. Sita, L. R. Angew. Chem., Int. Ed. 2009, 48, 2464-2472
52. Wei, J.; Zhang, W.; Sita, L. R. Angew. Chem., Int. Ed. 2010, 49, 1768-1772
53. Wei, J.; Zhang, W.; Wickham, R.; Sita, L. R. Angew. Chem., Int. Ed. 2010, 49, in press.
54. Stewart, P. J.; Blake, A. J.; Mountford, P. J. Organomet. Chem. 1998, 564, 209-214
55. Stewart, P. J.; Blake, A. J.; Mountford, P. Organometallics 1998, 17, 3271-3281
56. Guiducci, A. E.; Cowley, A. R.; Skinner, M. E. G.; Mountford, P. J. Chem. Soc., Dalton Trans. 2001, 1392-1394
57. Boyd, C. L.; Clot, E.; Guiducci, A. E.; Mountford, P. Organometallics 2005, 24, 2347-2367
58. Guiducci, A. E.; Boyd, C. L.; Mountford, P. Organometallics 2006, 25, 1167-1187
59. Guiducci, A. E.; Boyd, C. L.; Clot, E.; Mountford, P. J. Chem. Soc., Dalton Trans. 2009, 5960-5979
60. Hagadorn, J. R.; McNevin, M. J. Organometallics 2003, 22, 609-611
61. McNevin, M. J.; Hagadorn, J. R. Inorg. Chem. 2004, 43, 8547-8554
62. Sita, L. R.; Babcock, J. R. Organometallics 1998, 17, 5228-5230
63. Koterwas, L. A.; Fettinger, J. C.; Sita, L. R. Organometallics 1999, 18, 4183-4190
64. Babcock, J. R.; Incarvito, C.; Rheingold, A. L.; Fettinger, J. C.; Sita, L. R. Organometallics 1999, 18, 5729-5732
65. Details provided in the Supporting Information.
66. Fontaine, P. P.; Yonke, B. L.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2010, 132, 12273-12285
67. Brookhart, M.; Green, M. L. H.; Wong, L. L. Prog. Inorg. Chem. 1988, 36, 1-124
68. Scherer, W.; McGrady, G. S. Angew. Chem., Int. Ed. 2004, 43, 1782-1806
69. Brookhart, M.; Green, M. L. H.; Parkin, G. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 6908-6914
70. Hessen, B. J. Mol. Catal. A: Chem. 2004, 213, 129-135
71. Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Organometallics 2002, 21, 5122-5135
72. Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Angew. Chem., Int. Ed. 2001, 40, 2516-2519
73. You, Y.; Girolami, G. S. Organometallics 2008, 27, 3172-3180
74. Andes, C.; Harkins, S. B.; Murtuza, S.; Oyler, K.; Sen, A. J. Am. Chem. Soc. 2001, 123, 7423-7424
75. Briggs, J. R. J. Chem. Soc., Chem. Commun. 1989, 674-675
76. Dixon, J. T.; Green, M. J.; Hess, F. M.; Morgan, D. H. J. Organomet. Chem. 2004, 689, 3641-3668
77. Wass, D. F. Dalton Trans. 2007, 816 - 819 (review).
78. 2- iminoacyl complexes obtained through 1,1-insertion of isocyanides into metal-carbon bonds, see, for instance: Chamberlain, L. R.; Durfee, L. D.; Fanwick, P. E.; Kobriger, L.; Latesky, S. L.; McMullen, A. K.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 390-402
79. Durfee, L. D.; Rothwell, I. P. Chem. Rev. 1988, 88, 1059-1079
80. Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C.; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198-9210
81. Thorn, M. G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1999, 18, 4442-4447
82. Thorn, M. G.; Lee, J.; Fanwick, P. E.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 2002, 3398-3405
83. Sebastian, A.; Royo, P.; Gomez-Sal, P.; de Arellano, C. R. Eur. J. Inorg. Chem. 2004, 3814-3821
84. Spencer, L. P.; Fryzuk, M. D. J. Organomet. Chem. 2005, 690, 5788-5803
85. Thomson, R. K.; Schafer, L. L. Organometallics 2010, 29, 3546-3555
86. Bercaw, J. E.; Brintzinger, H. H. J. Am. Chem. Soc. 1971, 93, 2045-2046
87. Bercaw, J. E.; Marvich, R. H.; Bell, L. G.; Brintzinger, H. H. J. Am. Chem. Soc. 1972, 94, 1219-1238
88. McDade, C.; Green, J. C.; Bercaw, J. E. Organometallics 1982, 1, 1629-1634
89. Fandos, R.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 2665-2671
90. Hirotsu, M.; Fontaine, P. P.; Epshteyn, A.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2007, 129, 9284-9285
91. Hirotsu, M.; Fontaine, P. P.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2007, 129, 12690-12692