Chemistry of boryllithium: Synthesis, structure, and reactivity

Journal of the American Chemical Society

Volumn 130, Issue 47, 2008, Pages 16069-16079

  Segawa, Yasutomo ^a   Suzuki, Yuta ^a   Yamashita, Makoto ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC PHYSICS; ATOMS; BORON; BORON COMPOUNDS; CARBONYLATION; CHEMICAL SHIFT; CRYSTAL ATOMIC STRUCTURE; CRYSTALLOGRAPHY; DISSOLUTION; IONS; LITHIUM; METAL RECOVERY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SYNTHETIC FUELS; X RAY CRYSTALLOGRAPHY;

AIM ANALYSES; ALKYLLITHIUM; BORON ATOMS; CARBONYL GROUPS; CHEMICAL SHIFT ANISOTROPIES; CRYSTALLOGRAPHIC ANALYSES; HETEROCYCLE; INTRAMOLECULAR CYCLIZATION; LITHIUM SALTS; LONE PAIRS; MESITYL GROUPS; METAL EXCHANGES; METHYL CYCLOHEXANES; NITROGEN ATOMS; NMR CHEMICAL SHIFTS; NMR SPECTROSCOPIES; ORGANIC ELECTROPHILES; PHENYLLITHIUM; SOLID STATES; STRUCTURAL MODIFICATIONS; X-RAY CRYSTALLOGRAPHIES;

NONMETALS;

BORON; BORON DERIVATIVE; BORYLLITHIUM; CARBON; CARBON DIOXIDE; CARBON MONOXIDE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM SALT; METHYLCYCLOHEXANE; NITROGEN; PHENYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DISSOLUTION; ELECTRON TRANSPORT; INFRARED RADIATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SOLID STATE; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

EID: 56749150899     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8057919     Document Type: Article

References (101)

1. Wakefield, B. J. Organolithium methods; Academic Press: London, 1988.
2. N̈oth, H. In Science of Synthesis; Kaufmann, D. E., Matteson, D. S., Eds.; Georg Thieme Verlag: Stuttgart-New York, 2005; Vol. 6, pp 139-178.
3. Emsley, J. The Elements, 3rd ed.; Oxford University Press: New York, 1998.
4. Auten, R. W.; Kraus, C. A. J. Am. Chem. Soc. 1952, 74, 3398-3401.
5. Smith, K.; Swaminathan, K. J. Chem. Soc., Dalton Trans. 1976, 2297-2300.
6. Williams, J. L. R.; Doty, J. C.; Grisdale, P. J.; Searle, R.; Regan, T. H.; Happ, G. P.; Maier, D. P. J. Am. Chem. Soc. 1967, 89, 5153-5157.
7. Wilkey, J. D.; Schuster, G. B. J. Org. Chem. 1987, 52, 2117-2122.
8. Weber, L.; Schnieder, M.; Lonnecke, P. J. Chem. Soc., Dalton Trans. 2001, 3459-3464.
9. (a) Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 29, 982-983.
10. (b) Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47-53.
11. (c) Canesi, S.; Bouchu, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2004, 43, 4336-4338.
12. (d) Kabalka, G. W.; Wu, Z. Z.; Yao, M. L.; Natarajan, N. Appl. Radiat. Isot. 2004, 61, 1111-1115.
13. (e) Ciufolini, M. A.; Canesi, S.; Ousmer, M.; Braun, N. A. Tetrahedron 2006, 62, 5318-5337.
14. (f) Mun, S.; Lee, J. E.; Yun, J. Org. Lett. 2006, 8, 4887-4889.
15. (g) Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2008, 47, 145-147.
16. (h) Dang, L.; Lin, Z.; Marder, T. B. Organometallics 2008, 27, 4443-4454.
17. (a) Ito, H.; Kawakami, C.; Sawamura, M. J. Am. Chem. Soc. 2005, 127, 16034-16035.
18. (b) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M. J. Am. Chem. Soc. 2007, 129, 14856-14857.
19. (a) Laitar, D. S.; Mueller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196-17197.
20. (b) Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. J. Am. Chem. Soc. 2006, 128, 11036-11037.
21. (c) Zhao, H.; Lin, Z.; Marder, T. B. J. Am. Chem. Soc. 2006, 128, 15637-15643.
22. (d) Zhao, H.; Dang, L.; Marder, T. B.; Lin, Z. J. Am. Chem. Soc. 2008, 130, 5586-5594.
23. Most recently, asymmetric synthesis of α-amino boronate esters from aldimines was reported; see: (a) Beenan, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 5586-5594. 1,2-Diboration of aldimine using Pt catalyst has already been known, although the mechanism is unclear.
24. (b) Mann, G.; John, K. D.; Baker, R. T. Org. Lett. 2000, 2, 2105-2108.
25. 3 moiety at the backside of the C-I bond.
26. See: (b) Uemoto, T. Chem. Rev. 1996, 96, 1757-1778.
27. Blumenthal, A.; Bissinger, P.; Schmidbaur, H. J. Organomet. Chem. 1993, 462, 107-110.
28. Imamoto, T.; Hikosaka, T. J. Org. Chem. 1994, 59, 6753-6759.
29. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
30. Denk, M.; Lennon, R.; Hayashi, R.; West, R.; Belyakov, A. V.; Verne, H. P.; Haaland, A.; Wagner, M.; Metzler, N. J. Am. Chem. Soc. 1994, 116, 2691-2692.
31. Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F. R.; Bock, H.; Solouki, B.; Wagner, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1485-1488.
32. Gans-Eichler, T.; Gudat, D.; Nieger, M. Angew. Chem., Int. Ed. 2002, 41, 1888-1891.
33. (a) Schmidt, E. S.; Jockisch, A.; Schmidbaur, H. J. Am. Chem. Soc. 1999, 121, 9758-9759.
34. (b) Baker, R. J.; Farley, R. D.; Jones, C.; Kloth, M.; Murphy, D. M. J. Chem. Soc., Dalton Trans. 2002, 3844-3850.
35. Gallyl anions have been applied to coordination chemistry. See: (a) Jones, C.; Mills, D. P.; Rose, R. P.; Stasch, A. Dalton Trans. 2008, 4395-4408.
36. (b) Jones, C.; Rose, R. P.; Stasch, A. Dalton Trans. 2007, 2997-2999.
37. (c) Green, S. P.; Jones, C.; Mills, D. P.; Stasch, A. Organometallics 2007, 26, 3424-3430.
38. (d) Arnold, P. L.; Liddle, S. T.; McMaster, J.; Jones, C.; Mills, D. P. J. Am. Chem. Soc. 2007, 129, 5360-5361.
39. (e) Green, S. P.; Jones, C.; Lippert, K.-A.; Mills, D. P.; Stasch, A. Inorg. Chem. 2006, 45, 7242-7251.
40. (f) Aldridge, S.; Baker, R. J.; Coombs, N. D.; Jones, C.; Rose, R. P.; Rossin, A.; Willock, D. J. Dalton Trans. 2006, 3313-3320.
41. (g) Jones, C.; Mills, D. P.; Rose, R. P. J. Organomet. Chem. 2006, 691, 3060-3064.
42. (h) Jones, C.; Mills, D. P.; Platts, J. A.; Rose, R. P. Inorg. Chem. 2006, 45, 3146-3148.
43. (i) Baker, R. J.; Jones, C.; Mills, D. P.; Murphy, D. M.; Hey-Hawkins, E.; Wolf, R. Dalton Trans. 2006, 64-72.
44. (j) Baker, R. J.; Jones, C.; Murphy, D. M. Chem. Commun. 2005, 1339-1341.
45. (k) Baker, R. J.; Jones, C.; Kloth, M. Dalton Trans. 2005, 2106-2110.
46. (l) Baker, R. J.; Jones, C.; Kloth, M.; Platts, J. A. Organometallics 2004, 23, 4811-4813.
47. (m) Baker, R. J.; Jones, C.; Kloth, M.; Platts, J. A. Angew. Chem., Int. Ed. 2003, 43, 2660-2663.
48. (n) Baker, R. J.; Jones, C.; Platts, J. A. Dalton Trans. 2003, 3673-3674.
49. (o) Baker, R. J.; Jones, C.; Platts, J. A. J. Am. Chem. Soc. 2003, 125, 10534-10535.
50. (p) Baker, R. B.; Jones, C. Coord. Chem. Rev. 2005, 249, 1857-1869.
51. (a) Moezzi, A.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1992, 114, 2715-2717.
52. (b) Grigsby, W. J.; Power, P. P. Chem. Commun. 1996, 2235-2236.
53. (c) Grigsby, W. J.; Power, P. P. Chem. - Eur. J. 1997, 3, 368-375.
54. Power, P. P. Chem. Rev. 1999, 99, 3463-3503.
55. Sundermann, A.; Reiher, M.; Schoeller, W. W. Eur. J. Inorg. Chem. 1998, 305-310.
56. Metzler-Nolte, N. New J. Chem. 1998, 22, 793-795.
57. Brotherton, R. J.; McCloskey, A. L.; Petterson, L. L.; Steinberg, H. J. Am. Chem. Soc. 1960, 82, 6242-6245.
58. (a) Segawa, Y.; Yamashita, M.; Nozaki, K. Science 2006, 314, 113-115, This work was highlighted in the following references.
59. See: (b) Marder, T. B. Science 2006, 314, 64-70.
60. (c) Braunschweig, H. Angew. Chem., Int. Ed. 2007, 46, 1946-1948.
61. (a) Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. Chem. Lett. 2008, 37, 802-803.
62. (b) Segawa, Y.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2007, 46, 6710-6713.
63. Abrams, M. B.; Scott, B. L.; Baker, R. T. Organometallics 2000, 19, 4944-4956.
64. Burck, S.; Gudat, D.; Nieger, M.; Du Mont, W.-W. J. Am. Chem. Soc. 2006, 128, 3946-3955.
65. In a previous communication, we reported 82% yield. We have reexamined more carefully to prevent the decomposition of 35a with water and moisture to get 97% yield. Detail for the experimental procedure is described in the Supporting Information.
66. Weber, L.; Dobbert, E.; Stammler, H. G.; Neumann, B.; Boese, R.; Blaser, D. Chem. Ber. 1997, 130, 705-710.
67. Arduengo, A. J., III.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
68. Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
69. Korotkikh, N. I.; Raenko, G. F.; Pekhtereva, T. M.; Shvaika, O. P.; Cowley, A. H.; Jones, J. N. Russ. J. Org. Chem. 2006, 42, 1822-1833.
70. Kottke, T.; Sung, K. S.; Lagow, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1517-1519.
71. Arduengo, A. J.; Dixon, D. A.; Kumashiro, K. K.; Lee, C.; Power, W. P.; Zilm, K. W. J. Am. Chem. Soc. 1994, 116, 6361-6367.
72. Rath, N. P.; Fehlner, T. P. J. Am. Chem. Soc. 1988, 110, 5345-5349.
73. Del Bene, J. E.; Elguero, J. Magn. Reson. Chem. 2007, 45, 484-487.
74. 2- structure observed for alkyllithium species, which is less probable because of the bulky substituents on the boron center.
75. 6 in the gas phase was reported in the following reference: Onak, T. P.; Landesman, H.; Williams, R. E.; Shapiro, I. J. Phys. Chem. 1959, 63, 1533-1535.
76. 1, could not be optimized to the minimum.
77. Wagner, M.; van Eikema Hommes, N. J. R.; Nöth, H.; Schleyer, P. v. R. Inorg. Chem. 1995, 34, 607-614.
78. Lambert, C.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1129-1140.
79. Bader, R. F. W. Atoms In Molecules - A Quantum Theory; Oxford University Press: New York, 1990.
80. Bader, R. F. W. Chem. Rev. 1991, 91, 893-928.
81. This result is consistent with the fact that the previously reported AIM analyses on nonsolvated alkyllithiums have ionic C-Li bonds. See: (a) Bader, R. F. W.; Macdougall, P. J. J. Am. Chem. Soc. 1985, 107, 6788-6795.
82. (b) Ritchie, J. P.; Bachrach, S. M. J. Am. Chem. Soc. 1987, 109, 5909-5916.
83. N2 reaction of halomethylborane with benzyloxide followed by deprotection. See: Singh, R. P.; Matteson, D. S. J. Org. Chem. 2000, 65, 6650-6653.
84. Catalytic diboration of aldehyde to form α-borylalcohol was also reported. See, refs 11b and 11d.
85. Lithium alkoxides generated from N,N-dimethylformamide and carbyllithiums were reported to transfer a hydride to benzaldehyde or benzophenone in Oppenauer oxidation fashion. See: (a) Screttas, C. G.; Steele, B. R. J. Org. Chem. 1988, 53, 5151-5153. The related Mg-Oppenauer oxidation reactions were also reported.
86. See: (b) Meerwein, v. H.; Schmidt, R. Liebigs Ann. Chem. 1925, 444, 221-238.
87. (c) Byrne, B.; Karras, M. Tetrahedron Lett. 1987, 28, 769-772.
88. (d) Kloetzing, R. J.; Krasovskiy, A.; Knochel, P. Chem. - Eur. J. 2007, 13, 215-227.
89. Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. J. Am. Chem. Soc. 2007, 129, 9570-9571.
90. 2BC(=O)R′] has been postulated to dimerize to form a six-membered ring structure consisting of B, C, and O atoms. See: (a) Schmid, G.; Nöth, H. Chem. Ber. 1968, 101, 2502-2505.
91. Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050-2051.
92. 2Et has been proposed; however, there was no modern spectroscopic characterization. See ref 52.
93. (a) Base-stabilized esters have been widely explored, mainly as a boron analogue of α-amino acid derivatives with hydroborate structure Instead of α-carbon. See: Gabel, D.; El-Zaria, M. B. Product subclass 19: Carboxyboranes and Related Derivatives. In Science of Synthesis; Kaufmann, D. E., Matteson, D. S., Eds.; Georg Thieme Verlag: Stuttgart-New York, 2005; Vol. 6, pp 563-583.
94. (a) The structure was deposited to Cambridge Crystallographic Data Centre (CCDC-245188) as a private communication (2004) by Coppens, P., and Moncol, J.
95. (b) SDBSWeb: http://www.aist.go.jp/ RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, 2007/03/06).
96. Bruno, G.; Randaccio, L. Acta Crystallogr., Sect. B 1980, 36, 1711-1712.
97. Adams, J. M.; Morsi, S. E. Acta Crystallogr., Sect. B 1976, 32, 1345-1347.
98. Picard, J. P.; Calas, R.; Dunogues, J.; Duffaut, N.; Gerval, J.; Lapouyade, P. J. Org. Chem. 1979, 44, 420-424.
99. Steward, O. W.; Dziedzic, J. E.; Johnson, J. S. J. Org. Chem. 1971, 36, 3475-3480.
100. 6 were measured with commercially available chemicals.
101. Brook, A. G.; Abdesaken, F.; Gutekunst, G.; Plavac, N. Organometallics 1982, 1, 994-998.