Highly efficient organic reactions "on water", "in water", and both

Angewandte Chemie - International Edition

Volumn 47, Issue 15, 2008, Pages 2849-2852

  Shapiro, Nelly ^a   Vigalok, Arkadi ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Aldehydes; Green chemistry; Oxidation; Passerini reaction; Water

Indexed keywords

ALDEHYDES; CHEMICAL REACTIONS; CYANIDES; ESTERS; HYDROPHOBICITY; KETONES;

GREEN CHEMISTRY; OXIDATION; PASSERINI REACTION; WATER;

ORGANIC COMPOUNDS;

ALDEHYDE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; WATER;

EID: 42249084436     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705347     Document Type: Article

References (40)

1. For general references, see: a) Organic Synthesis in Water (Ed.: P. A. Grieco), Springer, New York, 1997;
2. b) Clean Solvents: Alternative Media for Chemical Reactions and Processing: ACS Symp. Ser. 2002, 819 (Eds.: M. A. Abraham, L. Moens);
3. c) Organic Reactions in Water (Ed.: U. M. Lindstroem), Blackwell, Oxford, UK, 2007;
4. d) H. C. Hailes, Org. Process Res. Dev. 2007, 11, 114.
5. a) P. Scrimin in Supramolecular Control of Structure and Reactivity (Ed.: A. Hamilton), Wiley, Chichester, UK, 1996, p. 101;
6. b) M. N. Khan, Micellar Catalysis, CRC Press, Boca Raton, USA, 2006.
7. For examples of homogeneous aqueous chemistry, see: a) W. Blokzijl, J. B. F. N. Engberts, J. Am. Chem. Soc. 1992, 114, 5440;
8. b) I. Vilotijevic, T. F. Jamison, Science 2007, 317, 1189;
9. c) see also: J. B. F. N. Engberts, M. J. Blandamer, Chem.Commun. 2001, 1701, and references therein.
10. a) M. C. Pirrung, K. Das Sarma, J.Am. Chem. Soc. 2004, 126, 444;
11. b) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3339;
12. Angew. Chem. Int. Ed. 2005, 44, 3275;
13. c) B. K. Price, J. M. Tour, J. Am. Chem. Soc. 2006, 128, 12899;
14. d) A. El-Batta, C. Jiang, W. Zhao, R. Anness, A. L. Cooksy, M. Bergdahl, J. Org. Chem. 2007, 72, 5244;
15. e) D. Gonzalez-Cruz, D. Tejedo, P. de Armas, F. Garcia-Tellado, Chem. Eur. J. 2007, 13, 4823;
16. key earlier work: f) D. C. Rideout, R. Breslow, J. Am. Chem. Soc. 1980, 102, 7816;
17. g) A. Lubineau, J. Org. Chem. 1986, 51, 2142.
18. a) J. R. McNesby, C. A. Heller, Chem. Rev. 1954, 54, 325 ;
19. b) S. S. Maslov, E. A. Blyumberg, Russian Chem. Rev. 1976, 45, 155;
20. c) L. Sajus, I. S. De Roch in Comprehensive Chemical Kinetics, Vol. 16 (Eds.: C. H. Bamford, C. F. H. Tipper), 1980, p. 89.
21. F. Koch in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, p. 427.
22. For detailed analysis of additives effect on aldehyde oxidation, see: a) C. Lehtinen, G. Brunow, Org. Process Res. Dev. 2000, 4, 544;
23. b) C. Lehtinen, V. Nevalainen, G. Brunow, Tetrahedron 2001, 57, 4741.
24. D. R. Larkin, J. Org. Chem. 1990, 55, 1563.
25. R. Battino, T. R. Rettich, T. Tominaga, J. Phys. Chem. Ref. Data 1983, 12, 163.
26. K. Buechner, H. Tummes, DE 1154454, 1963.
27. As the aldehyde oxidation reactions can be influenced by even trace amounts of metal (see for example: F. Loeker, W. Leitner, Chem. Eur. J. 2000, 6, 2011), the reactions were performed under strict metal-free conditions.
28. M. C. Pirrung, K. Das Sarma, Tetrahedron 2005, 61, 11456.
29. For additional references, see: a) A. R. Extance, D. W. M. Benzies, J. J. Morrish, QSAR Comb.Sci. 2006, 25, 484;
30. b) I. Kanizsai, Z. Szakonyi, R. Sillanpaa, F. Fulop, Tetrahedron Lett. 2006, 47, 9113.
31. For a general review on the Passerini reaction see: L. Banfi, R. Riva, Org. React. 2005, 65, 1.
32. For earlier comparison of "on water" versus "in water" Diels-Alder reactions, see: R. Breslow, U. Maitra, D. Rideout, Tetrahedron Lett. 1983, 24, 1901.
33. Considering the nasty nature of isocyanides, it was preferable to use a slight excess of the aldehyde rather than the isocyanide to achieve high conversions.
34. For the aldehyde/gem-diol equilibrium data, see: a) S. H. Hilal, L. L. Bornander, L. A. Carreira, QSAR Comb. Sci. 2005, 24, 631;
35. b) R. P. Bell, Adv. Phys. Org. Chem. 1966, 4, 1.
36. A dependence of aqueous phase multicomponent reactions on the mixing rate has been reported: M. C. Pirrung, Chem. Eur. J. 2006, 12, 1312.
37. For leading discussions on the effect of water in aqueous organic chemistry, see: a) R. Breslow, Acc. Chem. Res. 1991, 24, 159;
38. b) S. Otto, J. B. F. N. Engberts, Org. Biomol. Chem. 2003, 1, 2809;
39. c) Y. Jung, R. A. Marcus, J. Am. Chem. Soc. 2007, 129, 5492; also see Ref. [18].
40. The formation of gem-diols as intermediates in metal-catalyzed aldehyde oxidation in water has been proposed: M. Besson, P. Gallezot, Catal. Today 2000, 57, 127.