Density functional computations of Rh(I)-catalysed hydroacylation of acetic aldehyde and ethene

Molecular Simulation

Volumn 34, Issue 5, 2008, Pages 515-523

  Wang, Fen ^a   Meng, Qingxi ^b   Li, Ming ^c  

^a TAISHAN UNIVERSITY   (China)

^b SHANDONG AGRICULTURAL UNIVERSITY   (China)

^c SOUTHWEST UNIVERSITY   (China)

Author keywords

Acetic aldehyde; DFT; Ethene; Reaction mechanism; Rh catalysed hydroacylation

Indexed keywords

ABSORBED ENERGY; C C BOND FORMING REACTION; CARBONYL COMPLEXES; DENSITY FUNCTIONAL COMPUTATIONS; DENSITY-FUNCTIONAL (DF); HYDROACYLATION; OXIDATIVE ADDITION (OA); REACTION CHANNELS; TRANSFER REACTIONS; TRANSITION STATE (TS);

ADDITION REACTIONS; ALDEHYDES; CALCULATIONS; CARBONYLATION; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; ETHYLENE; FORMING; KETONES; ORGANIC COMPOUNDS; PROBABILITY DENSITY FUNCTION; RATE CONSTANTS; REACTION KINETICS; RHODIUM;

RHODIUM COMPOUNDS;

EID: 45849126831     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020701753635     Document Type: Article

References (37)

1. C. Jun and J.H. Lee, Application of C - H and C - C bond activation in organic synthesis, Pure. Appl. Chem. 76 (2004), p. 577.
2. C. Jia, T. Kitamura, and Y. Fujiwara, Catalytic functionalization of arenes and alkanes via C - H bond activation, Acc. Chem. Res. 34 (2001), p. 633.
3. F. Kakiuchi and S. Murai, Activation of C - H bonds: catalytic reactions, Top. Organomet. Chem. 3 (1999), p. 47.
4. Y. Guari, S. Sabo-Etienne, and B. Chaudret, Catalytic formation of carbon-carbon bonds by activation of carbon-hydrogen bonds, Eur. J. Inorg. Chem. 1999 (1999), p. 1047.
5. B.A. Arndtsen, R.G. Bergman, A. Mobley, and T.H. Peterson, Selective intermolecular carbon-hydrogen bond activation by synthetic metal complexes in homogeneous solution, Acc. Chem. Res. 28 (1995), p. 154.
6. A.E. Shilov and G.B. Shul′pin, Activation of C - H bonds by metal complexes, Chem. Rev. 97 (1997), p. 2879.
7. G. Dyker, Transition metal catalyzed coupling reactions under C - H activation, Angew. Chem. Int. Ed. 38 (1999), p. 1698.
8. V. Ritleng, C. Sirlin, and M. Pfeffer, Ru-, Rh-, and Pd-catalyzed C - C bond formation involving C - H activation and addition on unsaturated substrates: reactions and mechanistic aspects, Chem. Rev. 102 (2002), p. 1731.
9. J.A. Labinger and J.E. Bercaw, Understanding and exploiting C - H bond activation, Nature 417 (2002), p. 507.
10. F. Kakiuchi and S. Murai, Catalytic C - H/Olefin coupling, Acc. Chem. Res. 35 (2002), p. 826.
11. S.-I. Inoue, H. Takaya, K. Tani, S. Otsuka, T. Sato, and R. Noyori, Mechanism of the asymmetric isomerization of allylamines to enamines catalyzed by 2,2′-bis(diphenylphosphino)-1,1′binaphthyl-rhodium complexes, J. Am. Chem. Soc. 112 (1990), p. 4897.
12. S.H. Bergens and B. Bosnich, Homogeneous catalysis, Catalytic production of simple enols, J. Am. Chem. Soc. 113 (1991), p. 958.
13. R.W. Barnhart, X.-Q. Wang, P. Noheda, S.H. Bergens, J. Whelan, and B. Bosnich, Asymmetric catalysis. Asymmetric catalytic intramolecular hydroacylation of 4-pentenals using chiral Rhodium diphosphine catalysts, J. Am. Chem. Soc. 116 (1994), p. 1821.
14. C.-H. Jun, J.-B. Hong, and D.-Y. Lee, Chelation-assisted hydroacylation, Synlett (1999), p. 1.
15. A.D. Aloise, M.E. Layton, and M.D. Shair, Synthesis of cyclooctenones using intramolecular hydroacylation, J. Am. Chem. Soc. 122 (2000), p. 12610.
16. C.-H. Jun, J.-H. Chung, D.-Y. Lee, A. Loupy, and S. Chatti, Solvent-free chelation-assisted intermolecular hydroacylation: effect of microwave irradiation in the synthesis of ketone from aldehyde and 1-alkene by Rh(I) complex, Tetrahedron Lett. 42 (2001), p. 4803.
17. K. Tanaka and G.C. Fu, AVersatile new method for the synthesis of cyclopentenones via an unusual rhodium-catalyzed intramolecular trans hydroacylation of an alkyne, J. Am. Chem. Soc. 123 (2001), p. 11492.
18. M.C. Willis and S. Sapmaz, Intermolecular hydroacylation of acrylate esters: a new route to 1,4-dicarbonyls, Chem. Commun. (2001), p. 2558.
19. C.-H. Jun, C.W. Moon, and D.-Y. Lee, Chelation-assisted carbon-hydrogen and carbon-carbon bond activation by transition metal catalysts, Chem. Eur. J 8 (2002), p. 2423.
20. K. Tanaka, and G.C. Fu, Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones, J. Am. Chem. Soc. 125 (2003), p. 8078.
21. R.G. Parr and W. Yang, Density-functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
22. A.D. Becke, Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 98 (1993), p. 5648.
23. C. Lee, W. Yang, and R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37 (1988), p. 785.
24. B. Miehlich, A. Savin, H. Stoll, and H. Preuss, Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr, Chem. Phys. Lett. 157 (1989), p. 200.
25. A. Höllwarth, M. Böhme, S. Dapprich, A.W. Ehlers, A. Gobbi, K.F. Köhler, R. Stegmann, A. Veldkamp, and G. Frenking, A set of d-polarization functions for pseudo-potential basis sets of the main group elements Al-Bi and f-type polarization functions for Zn, Cd, Hg, Chem. Phys. Lett. 208 (1993), p. 237.
26. A.W.Ehlers,M.Böhme,S.Dapprich,A.Gobbi,A.Höllwarth,V.Jonas, K.F. Köhler, R. Stegmann, A. Veldkamp, and G. Frenking, A set of f-polarization functions for pseudo-potential basis sets of the transition metals Sc-Cu, Y-Ag and La-Au, Chem, Phys. Lett. 208 (1993), p. 111.
27. E.D. Glendening, A.E. Reed, J.E. Carpenter, and F. Weinhold, NBO Version 3.1
28. J.E. Carpenter and F. Weinhold, Analysis of the geometry of the hydroxymethyl radical by the "different hybrids for different spins" natural bond orbital procedure, J. Mol. Struct. (THEOCHEM) 169 (1988), p. 41.
29. J.P. Foster and F. Weinhold, Natural hybrid orbitals, J. Am. Chem. Soc. 102 (1980), p. 7211.
30. A.E. Reed and F. Weinhold, Natural bond orbital analysis of near-Hartree-Fock water dimmer, J. Chem. Phys. 78 (1983), p. 4066.
31. _, Vibrational-rotational energy transfer in collisions of HF (v = 4, J = 20) with rare gases, J. Chem. Phys. 78 (1983), p. 1736.
32. A.E. Reed, R.B. Weinstock, and F. Weinhold, Natural population analysis, J. Chem. Phys. 83 (1985), p. 735.
33. A.E. Reed, L.A. Curtiss, and F. Weinhold, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint, Chem. Rev. 88 (1988), p. 899.
34. F. Weinhold and J.E. Carpenter, The structure of small molecules and ions, Vol. 227, Plenum, New york, 1988.
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, J.T. Vreven, K.N. Kudin, J.C. Burant et al., Gaussian 03. Revision B.03, Gaussian, Inc., Pittsburgh PA, 2003.
36. R.F.W. Bader, Atoms in Molecules, A Quantum Theory; International Series of Monographs in Chemistry, Vol. 22, Oxford University Press, Oxford, UK, 1990.
37. F. Biegler-König, J. Schönbohm, R. Derdau, D. Bayles, and R.F.W. Bader, AIM 2000. Version 1, 2000.