Parallel ligand screening on olefin mixtures in asymmetric hydroformylation reactions

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3277-3280

  Cobley, Christopher J ^a   Klosin, Jerzy ^a   Qin, Cheng ^a   Whiteker, Gregory T ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYANIDE; PHOSPHITE; STYRENE; VINYL ACETATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HYDROFORMYLATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 4644234208     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0487938     Document Type: Article

References (19)

1. Claver, C.; van Leeuwen, P. W. N. M. In Rhodium Catalyzed Hydroformylation; Claver, C., van Leeuwen, P. W. N. M., Eds.; Kluwer Academic Publishers: Dordrecht, 2000.
2. Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A.; Petersen, J. L.; Abboud, K. A. J. Org. Chem. 2004, 69, 4031.
3. Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
4. (a) Gao, X.; Kagan, H. B. Chirality 1998, 10, 120.
5. (b) Wolf, C.; Hawes, P. A. J. Org. Chem. 2002, 67, 2727.
6. See Supporting Information for details.
7. (a) Babin, J. E.; Whiteker, G. T. Union Carbide U.S. Patent 5,360,938, 1994.
8. (b) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
9. The concentration of each olefin was held constant: 1.4 mM [styrene], 1.4 mM [vinyl acetate], 1.4 mM [allyl cyanide]. For reactions of individual olefins, the same olefin concentration was used.
10. Regioselectivities varied slightly presumably as a result of polarity differences between individual and combined olefins solutions.
11. Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413.
12. Data for Chiraphite were obtained from a separate set of comparative experiments.
13. Breeden, S.; Cole-Hamilton, D. J.; Foster, D. F.; Schwarz, G. J.; Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106.
14. Lu, S.; Li, X.; Wang, A. Catal. Today 2000, 63, 531. ABDPP = 1,6-anhydro-2,6-bis(diphenylphosphino)pyranose.
15. Reaction conditions: VA:Rh = 2000, neat VA (4 mL), temp = 60 °C, time = 10 h, 100% conversion.
16. Conversions obtained from experiments with separate olefins (see Supporting Information) are very similar to those obtained for the mixture of olefins.
17. (a) Turner, H.; Dales, G.; Vanerden, L.; Van Beek, J. Symyx Technologies Inc. U.S. Patent 6,306,658, 2001.
18. (b) Tuinstra, H. E.; Cummins, C. H. Adv. Mater. 2000, 12, 1819.
19. (c) Peil, K. P.; Neithamer, D. R.; Patrick, D. W.; Wilson, B. E.; Tucker, C. J. Macromol. Rapid Commun. 2004, 25, 119.