Substituent effects in the rhodium catalyzed hydroformylation of olefins using bis(diarylphosphino)methylamino ligands

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5967-5970

  Reetz, Manfred T ^a   Waldvogel, Siegfried R ^a   Goddard, Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030738615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01345-2     Document Type: Article

References (27)

1. Reetz, M. T.; Waldvogel, S. R. Angew. Chem. 1997, 109, 870; Angew. Chem., Int. Ed. Engl. 1997, 8, 865.
2. Reetz, M. T.; Waldvogel, S. R. Angew. Chem. 1997, 109, 870; Angew. Chem., Int. Ed. Engl. 1997, 8, 865.
3. 2 (R = (+)-bornyl) have been used in enantioselective hydroformylation reactions: Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. L. Appl. Organomet. Chem. 1993, 7, 513.
4. Waldvogel, S. R., Dissertation, Ruhr-Universität Bochum, 1996.
5. McAuliffe, C. A. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, 1987, Vol. 2, p 989.
6. Balch, A. L.; Olmstead, M. M.; Rowley, S. P. Inorg. Chim. Acta 1990, 168, 255; Fawcett, J.; Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. J.; Russel, D. R. J. Chem. Soc., Dalton Trans. 1993, 2563; Kellner, K.; Hanke, W. J. Organomet. Chem. 1987, 326, C9; Issleib, K.; Lischewski, M.; Zschunke, A. Z. Chem. 1974, 14, 243.
7. Balch, A. L.; Olmstead, M. M.; Rowley, S. P. Inorg. Chim. Acta 1990, 168, 255; Fawcett, J.; Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. J.; Russel, D. R. J. Chem. Soc., Dalton Trans. 1993, 2563; Kellner, K.; Hanke, W. J. Organomet. Chem. 1987, 326, C9; Issleib, K.; Lischewski, M.; Zschunke, A. Z. Chem. 1974, 14, 243.
8. Balch, A. L.; Olmstead, M. M.; Rowley, S. P. Inorg. Chim. Acta 1990, 168, 255; Fawcett, J.; Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. J.; Russel, D. R. J. Chem. Soc., Dalton Trans. 1993, 2563; Kellner, K.; Hanke, W. J. Organomet. Chem. 1987, 326, C9; Issleib, K.; Lischewski, M.; Zschunke, A. Z. Chem. 1974, 14, 243.
9. Balch, A. L.; Olmstead, M. M.; Rowley, S. P. Inorg. Chim. Acta 1990, 168, 255; Fawcett, J.; Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. J.; Russel, D. R. J. Chem. Soc., Dalton Trans. 1993, 2563; Kellner, K.; Hanke, W. J. Organomet. Chem. 1987, 326, C9; Issleib, K.; Lischewski, M.; Zschunke, A. Z. Chem. 1974, 14, 243.
10. 2 (1:1). Stirring is maintained at 60 °C. The kinetics are studied by taking frequent samples via HPLC valve and the contents examined by gas chromatography. The TOF values are determined by graphical means.
11. -3. Atomic coordinates and e.s.d.'s have been deposited at the Cambridge Crystallographic Data Centre.
12. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
13. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
14. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
15. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
16. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
17. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
18. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
19. See for example: Consiglio, G.; Pino, P. Top. Curr. Chem. 1982, 105, 77; Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007; Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597; Cornils, B.; Kuntz, E. G. J. Organomet. Chem. 1995, 502, 177; Broussard, M. E.; Juma, B., Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784; Lazzaroni, R.; Uccello-Barretta, G.; Scamuzzi, S; Settambolo, R.; Caiazzo, A. Organometallics 1996, 15, 4657; Ojima, I. Chem. Rev. 1988, 88, 1011; Simpson, M. C.; Currie, A. W. S.; Andersen, J.-A. M.; ColeHamilton, D. J.; Green, M. J. J. Chem. Soc., Dalton Trans. 1996, 1793.
20. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
21. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
22. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
23. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
24. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
25. 3 ligands, see: Oswald, A. A.; Hendriksen, D. E.; Kastrup, R. V.; Mozeleski, E. J. In Adv. Chem. Ser., Vol. 230 (Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R.; Slocum, D. W., Eds.); American Chemical Society: Washington, 1992, p 395.
26. Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703; Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2487.
27. Jacobsen, E. N.; Zhang, W.; Güler, M. L. J. Am. Chem. Soc. 1991, 113, 6703; Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2487.