Chemistry 'On Water'-Organic Synthesis in Aqueous Suspension

Organic Reactions in Water: Principles, Strategies and Applications

Volumn , Issue , 2007, Pages 350-365

  Narayan, Sridhar ^a   Fokin, Valery V ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Applications of the 'on water' method; Azodicarboxylates on water; Chemistry 'on water'; Other examples from our work; Perspective and conclusion

Indexed keywords

EID: 84890633748     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470988817.ch11     Document Type: Chapter

References (50)

1. Anastas, P.T. and Williamson, T.C., Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford University Press, Oxford, 1998.
2. Anastas, P.T., Heine, L.G. and Williamson, T.C. (Eds.), Green Chemical Syntheses and Processes, American Chemical Society,Washington, DC, 2000.
3. Matlack, A.S., Introduction to Green Chemistry, Marcel Dekker, New York, 2001.
4. Li, C.-J. and Chan, T.-H., Organic Reactions in Aqueous Media,Wiley, New York, 1997.
5. Grieco, P.A. (Ed.), Organic Synthesis in Water, Blackie, London, 1998.
6. Lindstrom, U.M., Stereoselective organic reactions in water, Chem. Rev., 2002, 102(8), 2751-2771.
7. Itami, K. and Yoshida, J.-I., The use of hydrophilic groups in aqueous organic reactions, Chem. Rec., 2002, 2(4), 213-224.
8. Narayan, S.,Muldoon, J., Finn, M.G., Fokin,V.V.,Kolb, H.C. and Sharpless, K.B., 'Onwater': unique reactivity of organic compounds in aqueous suspension, Angew. Chem. Int. Ed., 2005, 44(21), 3275-3279.
9. Kolb, H.C., Finn, M.G. and Sharpless, K.B., Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed., 2001, 40(11), 2004-2021.
10. Otto, S. and Engberts, J.B.F.N., Hydrophobic interactions and chemical reactivity, Org. Biomol. Chem., 2003, 1(16), 2809-2820.
11. Fringuelli, F., Piermatti, O., Pizzo, F. and Vaccaro, L., Ring opening of epoxides with sodium azide in water. A regioselective pH-controlled reaction, J. Org. Chem., 1999, 64(16), 6094-6096.
12. Rispens, T. and Engberts, J.B.F.N., A kinetic study of 1,3-dipolar cycloadditions in micellar media, J. Org. Chem., 2003, 68(22), 8520-8528.
13. van Mersbergen, D., Wijnen, J.W. and Engberts, J.B.F.N., 1,3-Dipolar cycloadditions of benzonitrile oxide with various dipolarophiles in aqueous solutions. A kinetic study, J. Org. Chem., 1998, 63(24), 8801-8805.
14. Wijnen, J.W., Steiner, R.A. and Engberts, J.B.F.N., 1,3-Dipolar cycloaddition of phenyl azide to norbornene in aqueous solutions, Tetrahedron Lett., 1995, 36(30), 5389-5392.
15. Sonntag, N.O.V., The reactions of aliphatic acid chlorides, Chem. Rev., 1953, 52(2), 237-416.
16. Padwa, A. (Ed.), 1,3-Dipolar Cycloaddition Chemistry,Wiley, New York, 1984.
17. Padwa, A. and Pearson, W.H. (Eds.), Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products,Wiley, New York, 2002.
18. Chuang,T.H. and Sharpless, K.B.,Applications of aziridinium ions. Selective syntheses ofß-aryl-a,ß-diamino esters, Org. Lett., 1999, 1(9), 1435-1437.
19. Chuang, T.H. and Sharpless, K.B.,Applications of aziridinium ions. Selective syntheses of a,ß-diamino esters, a-sulfanyl-ß-amino esters, ß-lactams, and 1,5-benzodiazepin-2-one, Org. Lett., 2000, 2(23), 3555-3557.
20. Chuang, T.H. and Sharpless, K.B., Applications of aziridinium ions: selective syntheses of pyrazolidin-3-ones and pyrazolo 1,2-a-pyrazoles, Helv. Chim. Acta, 2000, 83(8), 1734-1743.
21. Gajewski, J.J., Is the tert-butyl chloride solvolysis the most misunderstood reaction in organic chemistry? Evidence against nucleophilic solvent participation in the tert-butyl chloride transition state and for increased hydrogen bond donation to the 1-adamantyl chloride solvolysis transition state, J. Am. Chem. Soc., 2001, 123(44), 10877-10883.
22. Converso, A., Burow, K., Marzinzik, A., Sharpless, K.B. and Finn, M.G., 2,6-Dichloro-9- thiabicyclo[3.3.1]nonane: a privileged, bivalent scaffold for the display of nucleophilic components, J. Org. Chem., 2001, 66(12), 4386-4392.
23. Converso, A., Saaidi, P.L., Sharpless, K.B. and Finn, M.G., Nucleophilic substitution by Grignard reagents on sulfur mustards, J. Org. Chem., 2004, 69(21), 7336-7339.
24. Demko, Z.P. and Sharpless, K.B., Preparation of 5-substituted 1H-tetrazoles from nitriles in water, J. Org. Chem., 2001, 66(24), 7945-7950.
25. Schotten, C., The oxidation of piperidines, Chem. Ber., 1884, 21, 2544-2547.
26. Baumann, E., A method for the synthesis of benzoyl esters, Chem. Ber., 1886, 19, 3218-3222.
27. Georg, G.I., Boge, T.C., Cheruvallath, Z.S., Harriman, G.C.B., Hepperle, M. Park, H., et al., Schotten- Baumann acylation of N-debenzoyltaxol: an efficient route to N-acyl taxol analogues and their biological evaluation, Bioorg. Med. Chem. Lett., 1994, 4(2), 335-338.
28. Guss, C.O. and Rosenthal, R., Bromohydrins from olefins and N-bromosuccinimide in water, J. Am. Chem. Soc., 1955, 77(9), 2549.
29. Garner, P.P., Diels-Alder reactions in aqueous media, In: Grieco, P.A. (Ed.), Organic Synthesis in Water, Blackie, London, 1998, pp. 1-46.
30. Hopff, H. and Rautenstrauch, C.W., Production of addition products from dienes and compounds having an unsaturated carbon linkage activated by substituents, US Patent US 2262002, 1939.
31. Rideout, D.C. and Breslow, R., Hydrophobic acceleration of Diels-Alder reactions, J. Am. Chem. Soc., 1980, 102(26), 7816-7817.
32. Breslow, R.,Maitra,U. and Rideout,D., Selective Diels-Alder reactions in aqueous solutions and suspensions, Tetrahedron Lett. 1983, 24(18), 1901-1904.
33. Breslow, R., Hydrophobic effects on simple organic reactions in water. Acc. Chem. Res., 1991, 24(6), 159-164.
34. Grieco, P.A., Garner, P. and He, Z., Micellar catalysis in the aqueous intermolecular Diels-Alder reaction - rate acceleration and enhanced selectivity, Tetrahedron Lett., 1983, 24(18), 1897-1900.
35. Portmann, R., Process for preparing 1-substituted 4-cyano-1,2,3-triazoles,World PatentWO 9802423, 1998, Novartis AG.
36. Pirrung, M.C. and Das Sarma, K., Multicomponent reactions are accelerated in water, J. Am. Chem. Soc., 2004, 126(2), 444-445.
37. Pirrung, M.C. and Das Sarma, K., Aqueous medium effects on multi-component reactions, Tetrahedron, 2005, 61(48), 11456-11472.
38. Pirrung, M.C., Acceleration of organic reactions through aqueous solvent effects, Chem. Eur. J., 2006, 12(5), 1312-1317.
39. Ricci, A., Modern Amination Methods,Wiley-VCH,Weinheim, 2000.
40. Togni, A. and Grützmacher, H., CatalyticHeterofunctionalization: FromHydroamination toHydrozirconation, 1st edn.Wiley-VCH,Weinheim, 2001.
41. Leblanc,Y.,Zamboni, R. and Bernstein, M.A.,Amination of olefinic compoundswith bis(2,2,2-trichloroethyl) azodicarboxylate, J. Org. Chem., 1991, 56(5), 1971-1972.
42. Brimble, M.A. and Heathcock, C.H., Allylic amination by the Lewis-acid-mediated ene reaction of diethyl azodicarboxylate with alkenes, J. Org. Chem., 1993, 58(19), 5261-5263.
43. Brown, B.R., The Organic Chemistry of AliphaticNitrogen Compounds,OxfordUniversity Press, Oxford, 1994.
44. Rieber, N., Alberts, J., Lipsky, J.A. and Lemal, D.M. Δ1-1,2-Diazetines, J. Am. Chem. Soc., 1969, 91(20), 5668-5669.
45. Platz, R., Fuchs, W., Rieber, N., Samuel, U.-R. and Jung, J., Polycyclic nitrogen-containing compounds, German Patent DE 2615878, 1977, BASF AG.
46. Platz, R., Fuchs, W., Rieber, N. and Jung, J., Polycyclic nitrogen-containing compounds, German Patent DE 2742034, 1979, BASF AG.
47. Butler, R.N., Coyne, A.G., Cunningham, W.J., Moloney, E.M. and Burke, L.A., Water and the Hüisgen cycloaddition reaction: a focus on polar contributions to the transition state in the reactions of dicyano( phthalazinium)methanidewith substituted styrenes and benzylidene acetones,Helv. Chim. Acta, 2005, 88(7), 1611-1629.
48. Dambacher, J., Zhao,W., El-Batta, A., Anness, R., Jiang, C.C., and Bergdahl, M.,Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes, Tetrahedron Lett., 2005, 46(26), 4473-4477.
49. Postigo, A., Ferreri, C., Navacchia, M.L. and Chatgilialoglu, C., The radical-based reduction with (TMS)3SiH 'on water', Synlett, 2005, (18), 2854-2856.
50. Podgorsek, A., Stavber, S., Zupan, M. and Iskra, J., Visible light induced 'on water' benzylic bromination with N-bromosuccinimide, Tetrahedron Lett., 2006, 47(7), 1097-1099.