True metal-catalyzed hydroboration with titanium

Journal of the American Chemical Society

Volumn 118, Issue 7, 1996, Pages 1696-1702

  He, Xiaoming ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION;

EID: 0029985651     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9516773     Document Type: Article

References (65)

1. For the first example of a catalytic hydroboration with catecholborane see: Mannig, D.; Nöth, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 878.
2. For a review see: Burgess, K.; Ohlmeyer, M. J Chem. Rev. 1991, 91, 1179.
3. Westcott, S. A , Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863.
4. Brands, K. M.; Kende, A S. Tetrahedron Lett. 1992, 33, 5887.
5. Zhang, J.; Lou, B.; Guo, G.; Dai, L J. Org. Chem 1991, 56, 1670.
6. Evans, D. A.; Fu, G. C. J. Am. Chem. Soc. 1991, 113, 4042.
7. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1988, 110, 6917.
8. Evans, D. A.; Fu, G. C.; Hoveyda, A H. J. Am. Chem. Soc. 1992, 114, 6671.
9. Burgess, K.; Cassidy, J.; Ohlmeyer, M. J. J. Org. Chem. 1991, 56, 1020.
10. Burgess, K.; Ohlmeyer, M. J. Tetrahedron Lett. 1989, 30, 5857.
11. Burgess, K.; Ohlmeyer, M. J. Tetrahedron Lett. 1989, 30, 395.
12. Burgess, K.; Ohlmeyer, M J. J. Org. Chem. 1991, 56, 1027.
13. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426.
14. Sato, M.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1990, 31, 231.
15. Burgess, K.; van der Donk, W. A.; Ohlmeyer, M. J. Tetrahedron: Asymmetry 1991, 2, 613
16. Schnyder, A.; Hintermann, L.; Tosni, A. Angew. Chem., Int. Ed. Engal. 1995, 34, 931.
17. Gridnev, I. D.; Miyaura, N.; Suzuki, A. J Org. Chem. 1993, 58, 5351.
18. Evans, D. A.; Gage, J. R ; Leighton, J L. J Am. Chem. Soc. 1992, 114, 9434.
19. Kocienski, P., Jarowicki, K., Marczak, S. Synthesis 1991, 1191.
20. 3 has been shown to promote degradation of catecholborane, but in THF and at concentrations orders of magnitude greater than those employed in the experiments reported here. Westcott, S. A.; Blom., H. P.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Inorg. Chem. 1993, 32, 2175.
21. Burgess, K.; van der Donk, W. A ; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, G. C. J. Am. Chem. Soc. 1992, 114, 9350.
22. During the review of this manuscript Pereira and Srebmk reported alkyne hydroboration by pinacolborane catalyzed by Schwartz's reagent; Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127.
23. Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. A.: Chem. 1995, 95, 121.
24. Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813.
25. Bureess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616.
26. Burgess, K.; van der Donk, W. A. J. Am. Chem. Soc: 1994, 116, 6561.
27. 2 is not a true catalyst, but a catalyst precursor. Burgess's use of "true catalyst" refers to the difference between compounds involved in catalyzing catecholborane additions rather than catecholborane decomposition. Our use of true catalyst here referes to Burgess's distinction.
28. Harrison, K N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9221.
29. Sikora, D. J.; Moriarty, K J.; Rausch, M. D. In Inorganic Synthesis: Angelici, R. J., Ed.; John Wiley and Sons, Inc.: New York, 1990; Vol. 28, p 248.
30. Titanocene dicarbonyl is available from Strem.
31. Lane, C. F., Kabalka, G. W. Tetrahedron 1976, 32, 981.
32. Kool, L B.; Rausch, M. D., Ault, H. G.; Herberhold. M : Kremnitz, W. J. Organomet. Chem. 1985, 297, 159.
33. Tacke, M : Klein, C., Stufkens, D. J ; Oskam, A J. Organomet. Chem. 1993, 444, 75.
34. Motry, D. H.; Smith, M R J Am. Chem Soc 1995, 117, 6615.
35. Fachinetti, G.; Floriani, C., Marchetti, F.; Mellini, M. J. Chem. Soc., Dalton Trans. 1978, 1398.
36. Buchwald, S. L.; Nielson, R. B. Chem. Rev. 1988, 88, 1047
37. Cohen, S. A.; Auburn, P. R.; Bercaw, J. E J. Am. Chem. Soc. 1983, 105, 1136.
38. Hartwig, J. F.; Bhandari, S.; Rablen, P. R. J. Am. Chem. Soc. 1994, 116, 1839-1844.
39. Westcott, S. A.; Taylor, N. J.; Marder, T. B., Baker, R. T.; Jones, N. J.; Calabrese, J. C. J. Chem. Soc., Chem. Commun. 1991, 304.
40. Marsella, J. A.; Caulton, K. G. J. Am. Chem. Soc. 1982, 104, 2361.
41. Binger, P : Sandmeyer, F : Krüger, C.; Kuhnigk, J.; Goddard, R . Erker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 197
42. Hartwig, J. F.; De Gala, S. R. J. Am. Chem. Soc. 1994, 116, 3661.
43. Broene, R D.; Buchwald, S L. J. Am. Chem. Soc. 1993, 115, 12569
44. Nöth, H.; Voitländer, J.: Nussbaum, M. Naturwissenschaften 1960, 47, 57.
45. Pattiasina, J. W.; Heeres, H. J.: Bolhuis, F v., Meetsma, A., Teuben, J. H., Spek, A L. Organometallics 1987, 6, 1004.
46. Taube, R.; Böhme, P.; Gehrke, J. Z. Anorg. Allg Chem. 1989, 578, 89
47. Taube, R., Weckmann, E.; Bohme, P.; Behrke, J. Z. Anorg. Allg. Chem. 1989, 577, 245.
48. Matthews, K. D.; Kahwa, I. A.; Johnson, M. P.; Mague, J. T.; McPherson, G. L. Inorg. Chem. 1993, 32, 1442.
49. Hurlburt, P. K.; Anderson, O. P.; Strauss, S. H. J Am. Chem. Soc. 1991, 113, 6277.
50. Nakamura, H., Iitaka, Y.; Kitahara, T. J. Antibiot. 1977, 30, 714.
51. Berhalter, K.; Thewalt, U. J. Organomet Chem 1991, 420, 53.
52. Allmann, R.; Batzel, V.; Pfeil, R . Schmid, G Z. Naturforsch 1976, 31B, 1329.
53. Merola, J S ; Campo, K. S.; Gentile, R A , Modrick, M. A Inorg. Chim. Acta 1989, 165, 87.
54. Borkowsky, S. L.; Baenziger, N. C.; Jordan, R. F. Organometallics 1993, 12, 486.
55. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
56. Samuel, E.; Harrod, J. F.; Gourier, D.; Dromzee, Y.; Robert, F.; Jeannin, Y. Inorg. Chem. 1992, 31, 3252.
57. Clauss, A. W.; Wilson, S. R.; Buchanan, R. M.; Pierpont, C. G., Handrickson, D. N. Inorg. Chem. 1983, 22, 628.
58. Fachinetti, G.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Am. Chem. Soc. 1979, 101, 1767.
59. Sekutowski, D. G.; Stucky, G. D.; Inorg. Chem. 1975, 14, 2192
60. Thewalt, U.; Günther, T. J. Organomet. Chem. 1989, 379, 59.
61. Melmed, K. M.; Coucouvanis, D.; Lippard, S. J. Inorg. Chem. 1973, 12, 232.
62. Erskine, G. J.; Wilson, D. A.; McCowan, J. D J. Organomet. Chem. 1976, 114, 119.
63. Brown, H. C : Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249.
64. Cromer, D. T.; Waber, J. T. In The Kynoch Press: Birmingham, 1974; Vol. IV, Table 2.2 A.
65. Cromer, D. T.; Waber, J. T. In The Kynoch Press: Birmingham, 1974; Vol. IV.