PKa values of chiral Brønsted acid catalysts: Phosphoric acids/amides, sulfonyl/sulfuryl imides, and perfluorinated TADDOLs (TEFDDOLs)

Chemistry - A European Journal

Volumn 17, Issue 31, 2011, Pages 8524-8528

  Christ, Philipp ^b   Lindsay, Anita G ^a   Vormittag, Sonja S ^b   Neudörfl, Jörg M ^b,c   Berkessel, Albrecht ^b   O'Donoghue, Annmarie C ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF COLOGNE   (Germany)

^c X ray Crystallography ^*  (Germany)

Author keywords

acidity; chirality; fluorinated ligands; solvent effects; UV Vis spectroscopy

Indexed keywords

ACID CATALYST; FLUORINATED LIGANDS; GALILEO; ORGANOCATALYSIS; SOLVENT EFFECTS; STRONGEST ACID; TADDOLS; UV/ VIS SPECTROSCOPY;

AMINES; CATALYSTS; REACTION KINETICS; STEREOCHEMISTRY;

PHOSPHORIC ACID;

EID: 79960536604     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101157     Document Type: Article

References (40)

1. A. Berkessel, H. Gröger, Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005.
2. Enantioselective Organocatalysis: Reactions and Experimental Procedures (Ed.:, P. I. Dalko,), Wiley-VCH, Weinheim, 2007.
3. special issue on Organocatalysis (Ed.: B. List), Chem. Rev. 2007, 107, 5413-5415.
4. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
5. J. Woong Lee, T. H. Ryu, J. S. Oh, H. Y. Bae, H. Bin Jang, C. E. Song, Chem. Commun. 2009, 7224-7226.
6. J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416-14417.
7. Y. Zhu, J. P. Malerich, V. H. Rawal, Angew. Chem. 2010, 122, 157-160
8. Angew. Chem. Int. Ed. 2010, 49, 153-156.
9. D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 2001, 113, 96-142
10. Angew. Chem. Int. Ed. 2001, 40, 92-138.
11. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
12. Angew. Chem. Int. Ed. 2004, 43, 1566-1568.
13. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
14. C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246-9247.
15. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627.
16. P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. 2009, 121, 4427-4430
17. Angew. Chem. Int. Ed. 2009, 48, 4363-4366.
18. M. Treskow, J. Neudörfl, R. Giernoth, Eur. J. Org. Chem. 2009, 3693-3697.
19. A. Berkessel, P. Christ, N. Leconte, J.-M. Neudörfl, M. Schäfer, Eur. J. Org. Chem. 2010, 5165-5170.
20. T. Mutai, Y. Abe, K. Araki, J. Chem. Soc. Perkin Trans. 2 1997, 1805-1809.
21. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463.
22. I. M. Kolthoff, M. K. Chantoon, S. Bhowmik, J. Am. Chem. Soc. 1968, 90, 23-28.
23. C. D. Ritchie, R. E. Uschold, J. Am. Chem. Soc. 1967, 89, 1721-1725.
24. M. R. Crampton, I. A. Robotham, J. Chem. Res. Synop. 1997, 22-23.
25. I. A. Koppel, J. Koppel, P. Maria, J. Gal, R. Notario, V. M. Vlasov, R. W. Taft, Int. J. Mass Spectrom. Ion Processes 1998, 175, 61-69
26. I. A. Koppel, J. B. Koppel, F. Degerbeck, L. Grehn, U. Ragnarsson, J. Org. Chem. 1991, 56, 7172-7174
27. I. A. Koppel, J. Koppel, I. Leito, I. Koppel, M. Mishima, L. M. Yagupolskii, J. Chem. Soc. Perkin Trans. 2 2001, 229-232
28. I. A. Koppel, J. B. Koppel, V. O. Pihl, Org. React. 1988, 25, 77-101
29. I. A. Koppel, J. B. Koppel, L. I. Muuga, V. O. Pihl, Org. React. 1988, 25, 131-146.
30. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. Mccallum, G. J. Mccollum, N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 7006-7014.
31. F. G. Bordwell, J. C. Branca, D. L. Hughes, W. N. Olmstead, J. Org. Chem. 1980, 45, 3305-3313.
32. F. G. Bordwell, R. J. Mccallum, W. N. Olmstead, J. Org. Chem. 1984, 49, 1424-1427.
33. W. N. Olmstead, Z. Margolin, F. G. Bordwell, J. Org. Chem. 1980, 45, 3295-3299.
34. W. N. Olmstead, F. G. Bordwell, J. Org. Chem. 1980, 45, 3299-3305.
35. eq values, in the case of diphenylphosphoric acid 8.
36. a, the calcium content of the (in particular phosphoric) acids under scrutiny was shown by ICP-AAS to be negligible (see the Supporting Information).
37. CCDC-798769 (3 a), and 798770 (3 c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
38. Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008
39. H. Yamamoto, K. Futatsugi, in Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008, pp. 1-31.
40. 1-tBu) but in all cases the color of the solution changed rapidly. This may be due to nucleophilic attack at the pentafluorophenyl groups, for example, by the base or by the deprotonated fluoroalcohol itself. See also:, G. M. Brooke, J. Fluorine Chem. 1997, 86, 1-76.