Dehydrocoupling reactions of borane-secondary and -primary amine adducts catalyzed by group-6 carbonyl complexes: Formation of aminoboranes and borazines

Journal of the American Chemical Society

Volumn 131, Issue 41, 2009, Pages 14946-14957

  Kawano, Yasuro ^a   Uruichi, Mikio ^b,d   Shimoi, Mamoru ^a   Taki, Seitaro ^a   Kawaguchi, Takayuki ^a   Kakizawa, Taeko ^a,e   Ogino, Hiroshi ^b,c  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c OPEN UNIVERSITY OF JAPAN   (Japan)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^e KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CATALYST; AMINOBORANES; BORAZINE; CARBONYL COMPLEXES; CATALYTIC AMOUNTS; CATALYTIC DEHYDROGENATION; COMPUTATIONAL STUDIES; COVALENT BOND FORMATION; DEHYDROCOUPLING REACTIONS; DEHYDROCOUPLINGS; DFT CALCULATION; HIGH YIELD; METAL CARBONYL; MONOMERIC PRODUCTS; NMR SPECTROSCOPY; PHOTO-IRRADIATION; PRIMARY AMINES; REACTION MECHANISM;

AMINES; CARBONYLATION; CHROMIUM; DYES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; ORGANIC COMPOUNDS; SULFUR COMPOUNDS;

DEHYDROGENATION;

AMINE; AMINOBORANE DERIVATIVE; BORANE DERIVATIVE; BORAZINE DERIVATIVE; CARBONYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DEHYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOREACTIVITY; STOICHIOMETRY;

EID: 70350058974     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904918u     Document Type: Article

References (129)

1. (a) Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363.
2. (b) Clark, T. J.; Lee, K.; Manners, I. Chem. - Eur. J. 2006, 12, 8634.
3. (c) Hamilton, C. W.; Baker, R. T.; Staubitzc, A.; Manners, I. Chem. Soc. Rev. 2009, 38, 279.
4. Corey, J. Y. Adv. Organomet. Chem. 2004, 51, 1.
5. For example: (a) Aitken, C.; Harrod, J. F.; Malek, A.; Samuel, E. J. Organomet. Chem. 1988, 349, 285.
6. (b) Choi, N.; Tanaka, M. J. Organomet. Chem. 1998, 564, 81.
7. (c) Neale, N. R.; Tilley, T. D. J. Am. Chem. Soc. 2005, 127, 14745.
8. (d) Fermin, M. C.; Stephan, D. W. J. Am. Chem. Soc. 1995, 117, 12645.
9. (e) Böhm, V. P. W.; Brookhart, M. Angew. Chem., Int. Ed. 2001, 40, 4694.
10. (f) Waterman, R.; Tilley, T. D. Angew. Chem., Int. Ed. 2006, 45, 2926.
11. Jaska, C. A.; Manners, I. In Inorganic Chemistry in Focus II; Meyer, G., Naumann, D., Wesemann, L., Eds.; Wiley-VCH: Weinheim, 2005; pp 53-64.
12. Staubitz, A.; Soto, A. P.; Manners, I. Angew. Chem., Int. Ed. 2008, 47, 6212.
13. Denney, M. C.; Pons, V.; Hebden, T. J.; Heinekey, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 12048.
14. Keaton, R. J.; Blacquiere, J. M.; Baker, R. T. J. Am. Chem. Soc. 2007, 129, 1844.
15. Clark, T. J.; Whittell, G. R.; Manners, I. Inorg. Chem. 2007, 46, 7522.
16. Blaquiere, N.; Diallo-Garcia, S.; Gorelsky, S. I.; Black, D. A.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 14034.
17. Käss, M.; Friedrich, A.; Drees, M.; Schneider, S. Angew. Chem., Int. Ed. 2009, 48, 905.
18. Reviews of chemical hydrogen storage: (a) Grochala, W.; Peter, P.; Edwards, P. P. Chem. Rev 2004, 104, 1283.
19. (b) Marder, T. B. Angew. Chem., Int. Ed. 2007, 46, 8116.
20. 3 in ionic liquids: (a) Bluhm, M. E.; Bradley, M. G.; Butterrick, R., III.; Kusari, U.; Sneddon, L. G. J. Am. Chem. Soc. 2006, 128, 7748.
21. 3 through the action of acids: (b) Stephens, F. H.; Baker, R. T.; Matus, M. H.; Grant, D. J.; Dixon, D. A. Angew. Chem., Int. Ed. 2007, 46, 746.
22. 3 on mesoporous materials: (c) Gutowska, A.; Li, L.; Shin, Y.; Wang, C. M.; Li, X. S.; Linehan, J. C.; Smith, R. S.; Kay, B. D.; Schmid, B.; Shaw, W.; Gutowski, M.; Autrey, T. Angew. Chem., Int. Ed. 2005, 44, 3578.
23. Shimoi, M.; Nagai, S.; Ichikawa, M.; Kawano, Y.; Katoh, K.; Uruichi, M.; Ogino, H. J. Am. Chem. Soc. 1999, 121, 11704.
24. Kirtley, S. W.; Andrews, M. A.; Bau, R.; Grynkewich, G. W.; Marks, T. J.; Tipton, D. L.; Whittlesey, B. R. J. Am. Chem. Soc. 1977, 99, 7154.
25. Darensbourg, M. Y.; Bau, R.; Marks, M. W.; Burch, R. R., Jr.; Deaton, J. C.; Slater, S. J. Am. Chem. Soc. 1982, 104, 6961.
26. Wei, C.-Y.; Marks, M. W.; Bau, R.; Kirtley, S. W.; Bisson, D. E.; Henderson, M. E.; Koetzle, T. F. Inorg. Chem. 1982, 21, 2556.
27. (a) Katoh, K.; Shimoi, M.; Ogino, H. Inorg. Chem. 1992, 31, 670.
28. (b) Shimoi, M.; Katoh, K.; Ogino, H. J. Chem. Soc., Chem. Commun. 1990, 811.
29. For example, Toury, B.; Miele, P.; Cornu, D.; Vincent, H.; Bouix, J. Adv. Funct. Mater 2002, 12, 228.
30. Shimoi, M.; Katoh, K.; Uruichi, M.; Nagai, S.; Ogino, H. Current Topics in the Chemistry of Boron; Kabalka, G. W., Ed.; The Royal Society of Chemistry: London; 1994, pp 293-296.
31. Pons, V.; Denney, M. C.; Goldberg, K. I.; Heinekey, D. M. Prepr. Symp. Am. Chem. Soc. Div. Fuel Chem. 2005, 50, 51.
32. (a) Burg, A. B.; Randolph, C. L., Jr. J. Am. Chem. Soc. 1949, 71, 3451.
33. (b) Haubold, W.; Schaeffer, R. Chem. Ber. 1971, 104, 513.
34. (c) Nöth, H.; Vahrenkamp, H. Chem. Ber. 1967, 100, 3353.
35. (a) Storr, A.; Thomas, B. S.; Penland, A. D. J. Chem. Soc., Dalton Trans. 1972, 326.
36. (b) Nodie;th, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3070.
37. (c) Pasumansky, L.; Haddenham, D.; Clary, J. W.; Fisher, G. B.; Goralski, C. T.; Singaram, B. J. Org. Chem. 2008, 73, 1898.
38. (a) Narula, C. K.; Janik, J. F.; Duesler, E. N.; Paine, R. T.; Schaeffer, R. Inorg. Chem. 1986, 25, 3346.
39. (b) Campbell, G. W.; Johnson, L. J. Am. Chem. Soc. 1959, 81, 3800.
40. (c) Bissot, T. C.; Parry, R. W. J. Am. Chem. Soc. 1955, 77, 3481.
41. (d) Nöth, H.; Wrackmeyer, B. Chem. Ber. 1981, 114, 1150.
42. (a) Burg, A. B.; Randolph, C. L., Jr. J. Am. Chem. Soc. 1951, 73, 953.
43. (b) Ashby, E. C.; Kovar, R. A.; Culbertson, R. Inorg. Chem. 1971, 10, 900.
44. Phillips, W. D.; Miller, H. C.; Muetterties, E. L. J. Am. Chem. Soc. 1959, 81, 4496.
45. (a) Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. Chem. Commun. 2001, 962.
46. (b) Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424.
47. Sloan, M. E.; Clark, T. J.; Manners, I. Inorg. Chem. 2009, 48, 2429.
48. (a) Hough, W. V.; Schaeffer, G. W.; Dzurus, M.; Stewart, A. C. J. Am. Chem. Soc. 1955, 77, 864.
49. (b) Ashby, E. C.; Kovar, R. A. Inorg. Chem. 1971, 10, 1524.
50. Dietrich, B. L.; Goldberg, K. I.; Heinekey, D. M.; Autrey, T.; Linehan, J. C. Inorg. Chem. 2008, 47, 8583.
51. Schwartz, L. D.; Keller, P. C. J. Am. Chem. Soc. 1972, 94, 3015.
52. Kawano, Y.; Kakizawa, T.; Yamaguchi, K.; Shimoi, M. Chem. Lett. 2006, 35, 568.
53. Kakizawa, T.; Kawano, Y.; Shimoi, M. Organometallics 2001, 20, 3211.
54. Yasue, T.; Kawano, Y.; Shimoi, M. Angew. Chem., Int. Ed. 2003, 42, 1727.
55. Kawano, Y.; Hashiva, M.; Shimoi, M. Organometallics 2006, 25, 4420.
56. Shimoi, M.; Katoh, K.; Kodama, G.; Kawano, Y.; Ogino, H. J. Organomet. Chem. 2002, 659, 102.
57. 2 was isolated and structurally characterized. The cyclic aminoborane is ligated to the rhodium atom in a bidentate fashion in this compound. Douglas, T. M.; Chaplin, A. B.; Weller, A. S. J. Am. Chem. Soc. 2008, 130, 14432. This report also described the formation of a rhodiumdimethylamineborane complex and its intermediacy in the Rh-catalyzed borane dehydrocoupling reaction.
58. Nöth, H.; Vahrenkamp, H. Chem. Ber. 1966, 99, 1049.
59. Hall, R. E.; Schram, E. P. Inorg. Chem. 1971, 10, 192.
60. Niedenzu, K.; Dawson, J. W. Boron-Nitrogen Compounds; Academic Press Inc.: New York, 1965.
61. Beachley, O. T., Jr. Inorg. Chem. 1967, 6, 870.
62. Ryschkewitsch, G. E.; Wiggins, J. W. Inorg. Chem. 1970, 9, 314.
63. (a) Nguyen, M. T.; Nguyen, V. S.; Matus, M. H.; Gopakumar, G.; Dixon, D. A. J. Phys. Chem. A 2007, 111, 679.
64. (b) Li, Q. S.; Zhang, J.; Zhang, S. Chem. Phys. Lett. 2005, 404, 100.
65. x. (a) Smith, R. S.; Kay, B. D.; Schmid, B.; Li, L.; Hess, N.; Gutowski, M.; Autrey, T. Prep. Pap.- Am. Chem. Soc., Div. Fuel Chem. 2005, 50, 112.
66. (b) Stowe, A. C.; Shaw, W. J.; Linehan, J. C.; Schmid, B.; Autrey, T. Phys. Chem. Chem. Phys. 2007, 9, 1831.
67. Chen, Y.; Fulton, J. L.; Linehan, J. C.; Autrey, T. J. Am. Chem. Soc. 2005, 127, 3254.
68. In a recent review, they mentioned the possibility of an intramolecular mechanism. Clark, T. J.; Lee, K.; Manners, I. Chem. Eur. J. 2006, 12, 8634.
69. (a) Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 1334.
70. (b) Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 9776.
71. (c) Jaska, C. A.; Clark, T. J.; Clendenning, S. B.; Grozea, D.; Turak, A.; Lu, Z.-H.; Manners, I. J. Am. Chem. Soc. 2005, 127, 5116.
72. Fulton, J. F.; Linehan, J. C.; Autrey, T.; Balasubramanian, M.; Chen, Y.; Szymczak, N. K. J. Am. Chem. Soc. 2007, 129, 11936.
73. Clark, T. J.; Russell, C. A.; Manners, I. J. Am. Chem. Soc. 2006, 128, 9582.
74. Luo, Y.; Ohno, K. Organometallics 2007, 26, 3597.
75. Pun, D.; Lobkovsky, E.; Chirik, P. J. Chem. Commun. 2007, 3297.
76. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
77. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
78. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
79. Selected papers for M⋯HX hydrogen bonds: (a) Brammer, L.; McCann, M. C.; Bullock, R. M.; McMullan, R. K.; Sherwood, P. Organometallics 1992, 11, 2339.
80. (b) Roe, D. M.; Bailey, P. M.; Moseley, K.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1972, 1273.
81. (a) Matthews, S. L.; Pons, V.; Heinekey, D. M. J. Am. Chem. Soc. 2005, 127, 850.
82. (b) Sweany, R. L. J. Am. Chem. Soc. 1985, 107, 2374.
83. (c) Upmacis, R. K.; Gadd, G. E.; Poliakoff, M.; Simpson, M. B.; Turner, J. J.; Whyman, R.; Simpson, A. F. J. Chem. Soc., Chem. Commun. 1985, 27.
84. (d) Church, S. P.; Grevels, F.-W.; Hermann, H.; Schaffner, K. J. Chem. Soc., Chem. Commun. 1985, 30.
85. Quite recently, a related zirconocene-amidoborane complex was isolated and structurally characterized. Forster, T. D.; Tuononen, H. M.; Parvez, M.; Roesler, R. J. Am. Chem. Soc. 2009, 131, 6689.
86. Harder's amidoborane calcium compound is also relevant. Spielmann, J.; Harder, S. J. Am. Chem. Soc. 2009, 131, 5064. In addition, a lutetium iminestabilized borane complex, which was reported by Roesky and coworkers very recently, has structural relevance.
87. Meyer, N.; Jenter, J.; Roesky, P. W.; Eickerling, G.; Scherer, W. Chem. Commun. 2009, 4693.
88. Fletcher, T. R.; Rosenfeld, R. N. J. Am. Chem. Soc. 1985, 107, 2203.
89. 6] has been suggested. Fletcher, T. R.; Rosenfeld, R. N. J. Am. Chem. Soc. 1985, 107, 2203.
90. Labile nature of borane ligands has been confirmed experimentally. Kawano, Y.; Yamaguchi, K.; Miyake, S.; Kakizawa, T.; Shimoi, M. Chem. - Eur. J. 2007, 13, 6920.
91. Paul, A.; Musgrave, C. B. Angew. Chem., Int. Ed. 2007, 46, 8153.
92. Denis, J.-M.; Fointos, H.; Szelke, H.; Toupet, L.; Pham, T.-N.; Madec, P.-J.; Gaumont, A.-C. Chem. Commun. 2003, 54.
93. Bakhmutov, V. I. Dihydrogen Bond, Principles, Experiments, and Applications; Wiley-VCH: New York, 2008.
94. Selected papers for dihydrogen bond: (a) Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348.
95. (b) Crabtree, R. H. Science 1998, 282, 2000.
96. (c) Bosque, R.; Maseras, F.; Eisenstein, O.; Patel, B. P.; Yao, W.; Crabtree, R. H. Inorg. Chem. 1997, 36, 5505.
97. (d) Lee, J. C., Jr.; Peris, E.; Rheingold, A. L.; Crabtree, R. H. J. Am. Chem. Soc. 1994, 116, 11014.
98. (e) Xu, W.; Lough, A. J.; Morris, R. H. Inorg. Chem. 1996, 35, 1549.
99. Nöth, H.; Thomas, S. Eur. J. Inorg. Chem. 1999, 1373.
100. In crystal, free 1a adopts a chain-like structure, in which amineborane molecules are linked by BH⋯HN interactions. Molecules of primary adduct 1g are linked in ribbons. Aldridge, S.; Downs, A. J.; Tang, C. Y.; Parsons, S.; Clarke, M. C.; Johnstone, R. D. L.; Robertson, H. E.; Rankin, D. W. H.; Wann, D. A. J. Am. Chem. Soc. 2009, 131, 2231.
101. Dorn, H.; Singh, R. A.; Massey, J. A.; Nelson, J. M.; Jaska, C. A.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2000, 122, 6669. This paper also reported Rh-catalyzed dehydrocoupling reactions of phosphine boranes.
102. Jaska, C. A.; Lough, A. J.; Manners, I. Inorg. Chem. 2004, 43, 1090.
103. (a) Tague, T. J., Jr.; Andrews, L. J. Am. Chem. Soc. 1994, 116, 4970.
104. (b) Watts, J. D.; Bartlett, R. J. J. Am. Chem. Soc. 1995, 117, 825.
105. (c) Schreiner, P. R.; Schaefer, H. F.; Schleyer, P. v. R. J. Chem. Phys. 1994, 101, 7625.
106. - structure. Filippov, O. A.; Filin, A. M.; Tsupreva, V. N.; Belkova, N. V.; Lledós, A.; Ujaque, G.; Epstein, L. M.; Shubina, E. S. Inorg. Chem. 2006, 45, 3086.
107. 2. Luo, Y.; Ohno, K. Organometallics 2007, 26, 3597.
108. (a) Bonham, J.; Drago, R. S. Inorg. Synth. 1967, 9, 8.
109. (b) Nöth, H.; Beyer, H. Chem. Ber. 1960, 93, 928.
110. (c) Kelly, H. C.; Marchelli, F. R.; Giusto, M. B. Inorg. Chem. 1964, 3, 431.
111. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
112. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
113. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
114. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
115. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
116. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
117. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
118. (a) Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
119. (b) Lynch, B. J.; Truhlar, D. G. J. Phys. Chem. A 2001, 105, 2936.
120. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
121. 2 ligand interacted with a carbonyl oxygen atom instead of the chromium center.
122. Fukui, K. Acc. Chem. Res. 1981, 14, 363.
123. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
124. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
125. (a) Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H.; Schwerdtfeger, P.; Pitzer, R. M. Mol. Phys. 1993, 78, 1211.
126. (b) Kuechle, W.; Dolg, M.; Stoll, H.; Preuss, H. J. Chem. Phys. 1994, 100, 7535.
127. (c) Leininger, T.; Nicklass, A.; Stoll, H.; Dolg, M.; Schwerdtfeger, P. J. Chem. Phys. 1996, 105, 1052.
128. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
129. Frisch, M. J.; et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford CT, 2004.