The metal-ligand bifunctional catalysis: A theoretical study on the ruthenium(II)-catalyzed hydrogen transfer between alcohols and carbonyl compounds

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1466-1478

  Yamakawa, Masashi ^a   Ito, Hisashi ^b   Noyori, Ryoji ^b  

^a KINJO GAKUIN UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBONYL DERIVATIVE; FORMALDEHYDE; LIGAND; METAL; METHANOL; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; ENERGY; HYDROGEN BOND; HYDROGENATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033999757     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991638h     Document Type: Article

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99. The values in parentheses have been obtained by B3LYP.
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114. For the notation of the absolute configuration, see: (a) Lecomte, C.; Dusausoy, Y.; Protas, J.; Tirouflet, J.; Dormond, A. J. Organomet. Chem. 1974, 73, 67. (b) Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
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118. Yamada, I.; Noyori, R. unpublished.
119. Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
120. For example, see: (a) Klob, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (b) Jacobsen, E. N. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G.; Wilkinson, G. Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 11.1.
121. For example, see: (a) Klob, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. (b) Jacobsen, E. N. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G.; Wilkinson, G. Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 11.1.
122. (a) Rosenberg, B.; Van Camp, L.; Grimley, E. B.; Thomson, A. J. J. Biol. Chem. 1967, 242, 1347.
123. (b) Reedijk, J. Inorg. Chim. Acta, 1992, 198-200, 873.
124. For a similar phenomenon in the Ru-catalyzed hydrogenation, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996 61, 4872. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
125. For a similar phenomenon in the Ru-catalyzed hydrogenation, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996 61, 4872. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
126. For a similar phenomenon in the Ru-catalyzed hydrogenation, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996 61, 4872. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
127. For a similar phenomenon in the Ru-catalyzed hydrogenation, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996 61, 4872. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
128. For a similar phenomenon in the Ru-catalyzed hydrogenation, see: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996 61, 4872. (d) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529. (e) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.
129. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; Wiley: New York, 1981.
130. Corey, E. J.; Helal, C. J. Tetrahedron Lett. 1995, 56, 9153.
131. (a) Nishio, M.; Hirota, M. Tetrahedron 1989, 45, 7201.
132. (b) Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction, Evidence, Nature, and Consequences; Wiley-VCH: New York, 1998.
133. Very recently, a similar mechanistic conclusion was derived by a Swedish group: Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.