Complexation of Lewis acid with trialkylcopper(III): On the origin of BF3-aceeleration of cuprate conjugate addition [13]

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1826-1827

  Nakamura, Eiichi ^a   Yamanaka, Masahiro ^a   Mori, Seiji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; COPPER COMPLEX; ORGANOMETALLIC COMPOUND;

CHEMICAL BOND; COMPLEX FORMATION; CONJUGATE; ENERGY TRANSFER; LETTER; LIGAND BINDING; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0034054974     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993124o     Document Type: Letter

References (22)

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4. Smith, A. B., III.; Jerris, P. J. J. Am. Chem. Soc. 1981, 103, 194-195. Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349-362.
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7. (a) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 4900-4910.
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11. All calculations were performed with GAUSSIAN 94 package, and details are described in Supporting Information. The geometry optimization was performed at the B3LYP level with the basis set denoted as 631A consisting of Ahlrichs-SVP all-electron basis set for the Cu atom and 6-31G-(d) for the rest. Equilibrium (local minima) and transition-state structures have zero and one imaginary frequency, respectively. In some cases, the energies were evaluated at the CCSD(T) level. Electron population was calculated by natural population analysis, see: Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
12. 3Cu(III) 4 (C, symmetry assumed) has a very small negative eigenvalue.
13. (b) Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025-11026.
14. Bera, J. K.; Samuelson, A. G.; Chandrasekhar, J. Organometallics 1998, 17, 4136-4145.
15. For Au(III) species, see: Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255-7265. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1977, 99, 8440-8447.
16. For Au(III) species, see: Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255-7265. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1977, 99, 8440-8447.
17. Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
18. Neumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
19. 2 (Supporting Information).
20. For different interpretation of this magnitude of the stabilization energy, see: Bertz, S. H.; Miao, G.; Rossiter, B. E.; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023-11024.
21. Such consideration may be in consonance with the spectacular success of the Feringa ligand: Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; Vries, A. H. M. de Angew. Chem., Int. Ed. Engl. 1997, 36, 2621-2623.
22. For 3D structures and coordinates, see: http://www.chem.s.u-tokyo.ac.jp/~common/Theo/BF3/title.