Recyclable Lewis acid catalysts by tuning supercritical vs liquid carbon dioxide phases: Lanthanide catalysts with tris(perfluorooctanesulfonyl)methide and bis(perfluorooctanesulfonyl)amide

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8345-8349

  Nishikido, Joji ^a   Kamishima, Mayumi ^a   Matsuzawa, Hiroshi ^b   Mikami, Koichi ^b  

^a NOGUCHI INSTITUTE   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bis(perfluorooctanesulfonyl) amide; Environmental benignity; Lanthanide; Lewis acid catalysis; Liquid carbon dioxide; Supercritical carbon dioxide; Tris(perfluorooctanesulfonyl)methide

Indexed keywords

BIS(PERFLUOROOCTANESULFONYL)AMIDE; CARBON DIOXIDE; LANTHANIDE; LEWIS ACID; TRIS(PERFLUOROOCTANESULFONYL)METHIDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; ESTERIFICATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SUPERCRITICAL FLUID; TEMPERATURE DEPENDENCE;

EID: 0037037898     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00986-9     Document Type: Article

References (48)

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32. For Lewis acid catalyzed reactions in supercritical fluids, see: (a) Komoto I., Kobayashi S. Org. Lett. 4:2002;1115 (b) Fukuzawa S.-I., Metoki K., Komuro Y., Funazukuri T. Synlett. 2002;134 (c) Komoto I., Kobayashi S. Chem. Commum. 2001;1842 (d) Fukuzawa S.-I., Matsuzawa H., Metoki K. Synlett. 2001;709 (e) Tsuchiya T., Odashima K., Kobayashi S. Chem. Lett. 2000;178 (f) Kawada A., Mitamura S., Matsuo J.-I., Tsuchiya T., Kobayashi S. Bull. Chem. Soc. Jpn. 73:2000;2325 (g) Mikami K., Matsukawa S., Kayaki Y., Ikariya T. Tetrahedron Lett. 41:2000;1931 (h) Oakes R.S., Heppenstall T.J., Shezad N., Clifford A.A., Rayner C.M. Chem. Commum. 1999;1459.
33. For Lewis acid catalyzed reactions in supercritical fluids, see: (a) Komoto I., Kobayashi S. Org. Lett. 4:2002;1115 (b) Fukuzawa S.-I., Metoki K., Komuro Y., Funazukuri T. Synlett. 2002;134 (c) Komoto I., Kobayashi S. Chem. Commum. 2001;1842 (d) Fukuzawa S.-I., Matsuzawa H., Metoki K. Synlett. 2001;709 (e) Tsuchiya T., Odashima K., Kobayashi S. Chem. Lett. 2000;178 (f) Kawada A., Mitamura S., Matsuo J.-I., Tsuchiya T., Kobayashi S. Bull. Chem. Soc. Jpn. 73:2000;2325 (g) Mikami K., Matsukawa S., Kayaki Y., Ikariya T. Tetrahedron Lett. 41:2000;1931 (h) Oakes R.S., Heppenstall T.J., Shezad N., Clifford A.A., Rayner C.M. Chem. Commum. 1999;1459.
34. For Lewis acid catalyzed reactions in supercritical fluids, see: (a) Komoto I., Kobayashi S. Org. Lett. 4:2002;1115 (b) Fukuzawa S.-I., Metoki K., Komuro Y., Funazukuri T. Synlett. 2002;134 (c) Komoto I., Kobayashi S. Chem. Commum. 2001;1842 (d) Fukuzawa S.-I., Matsuzawa H., Metoki K. Synlett. 2001;709 (e) Tsuchiya T., Odashima K., Kobayashi S. Chem. Lett. 2000;178 (f) Kawada A., Mitamura S., Matsuo J.-I., Tsuchiya T., Kobayashi S. Bull. Chem. Soc. Jpn. 73:2000;2325 (g) Mikami K., Matsukawa S., Kayaki Y., Ikariya T. Tetrahedron Lett. 41:2000;1931 (h) Oakes R.S., Heppenstall T.J., Shezad N., Clifford A.A., Rayner C.M. Chem. Commum. 1999;1459.
35. For Lewis acid catalyzed reactions in supercritical fluids, see: (a) Komoto I., Kobayashi S. Org. Lett. 4:2002;1115 (b) Fukuzawa S.-I., Metoki K., Komuro Y., Funazukuri T. Synlett. 2002;134 (c) Komoto I., Kobayashi S. Chem. Commum. 2001;1842 (d) Fukuzawa S.-I., Matsuzawa H., Metoki K. Synlett. 2001;709 (e) Tsuchiya T., Odashima K., Kobayashi S. Chem. Lett. 2000;178 (f) Kawada A., Mitamura S., Matsuo J.-I., Tsuchiya T., Kobayashi S. Bull. Chem. Soc. Jpn. 73:2000;2325 (g) Mikami K., Matsukawa S., Kayaki Y., Ikariya T. Tetrahedron Lett. 41:2000;1931 (h) Oakes R.S., Heppenstall T.J., Shezad N., Clifford A.A., Rayner C.M. Chem. Commum. 1999;1459.
36. Koppel and Taft et al. have reported the gas phase acidities of a variety of super acids: Bis(trifluoromethanesulfonyl)amine is stronger than trifluofomethanesulfonic acid by G=7.7kcal/mol and tris(trifluoromethanesulfonyl)methane is stronger than bis(trifluoromethanesulfonyl)amine by G=2.8kcal/mol. They have also reported that bis(perfluorobutanesulfonyl)amine is stronger than bis(trifluoromethanesulfonyl)amine by G=7.7kcal/mol: J. Am. Chem. Soc., 1994, 116, 3047.
37. 3: (a) Mikami K., Mikami Y., Matsuzawa H., Matsumoto Y., Nishikido J., Yamamoto F., Nakajima H. Tetrahedron. 58:2002;4015 (b) Mikami K., Mikami Y., Matsumoto Y., Nishikido J., Yamamoto F., Nakajima H. Tetrahedron Lett. 42:2001;289.
38. 3: (a) Mikami K., Mikami Y., Matsuzawa H., Matsumoto Y., Nishikido J., Yamamoto F., Nakajima H. Tetrahedron. 58:2002;4015 (b) Mikami K., Mikami Y., Matsumoto Y., Nishikido J., Yamamoto F., Nakajima H. Tetrahedron Lett. 42:2001;289.
39. (a) Barrett A.G.M., Boulec N., Braddock D.C., Catterick D., Chadwick D., White A.J.P., Williams D.J. Tetrahedron. 58:2002;3835.
40. (b) Barrett A.G.M., Braddock D.C., Ducray R., McKinnell R.M., Waller F.J. Synlett. 2000;317.
41. Water/supercritical fluids biphase reaction has been already reported, but fluorous/supercritical fluids biphase reaction is not still reported. For water/supercritical fluids biphase reaction, see; (a) Bonilla R.J., James B.R., Jessop P.G. Chem. Commum. 2000;941 (b) Jacobson G.B., Lee C.T. Jr., Johnston K.P., Tumas W. J. Am. Chem. Soc. 121:1999;11902 (c) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Chem. Commum. 1999;1277 (d) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Tetrahedron Lett. 40:1999;6427.
42. Water/supercritical fluids biphase reaction has been already reported, but fluorous/supercritical fluids biphase reaction is not still reported. For water/supercritical fluids biphase reaction, see; (a) Bonilla R.J., James B.R., Jessop P.G. Chem. Commum. 2000;941 (b) Jacobson G.B., Lee C.T. Jr., Johnston K.P., Tumas W. J. Am. Chem. Soc. 121:1999;11902 (c) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Chem. Commum. 1999;1277 (d) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Tetrahedron Lett. 40:1999;6427.
43. Water/supercritical fluids biphase reaction has been already reported, but fluorous/supercritical fluids biphase reaction is not still reported. For water/supercritical fluids biphase reaction, see; (a) Bonilla R.J., James B.R., Jessop P.G. Chem. Commum. 2000;941 (b) Jacobson G.B., Lee C.T. Jr., Johnston K.P., Tumas W. J. Am. Chem. Soc. 121:1999;11902 (c) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Chem. Commum. 1999;1277 (d) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Tetrahedron Lett. 40:1999;6427.
44. Water/supercritical fluids biphase reaction has been already reported, but fluorous/supercritical fluids biphase reaction is not still reported. For water/supercritical fluids biphase reaction, see; (a) Bonilla R.J., James B.R., Jessop P.G. Chem. Commum. 2000;941 (b) Jacobson G.B., Lee C.T. Jr., Johnston K.P., Tumas W. J. Am. Chem. Soc. 121:1999;11902 (c) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Chem. Commum. 1999;1277 (d) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Tetrahedron Lett. 40:1999;6427.
45. Water/supercritical fluids biphase reaction has been already reported, but fluorous/supercritical fluids biphase reaction is not still reported. For water/supercritical fluids biphase reaction, see; (a) Bonilla R.J., James B.R., Jessop P.G. Chem. Commum. 2000;941 (b) Jacobson G.B., Lee C.T. Jr., Johnston K.P., Tumas W. J. Am. Chem. Soc. 121:1999;11902 (c) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Chem. Commum. 1999;1277 (d) Bhanage B.M., Ikushima Y., Shirai M., Arai M. Tetrahedron Lett. 40:1999;6427.
46. Recently, fluorous catalysts were revised as solids in organic solvent; (a) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (b) Ishihara, K.; Kondo, S.; Yamamoto, H. Synlett 2001, 1391.
47. Recently, fluorous catalysts were revised as solids in organic solvent; (a) Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490. (b) Ishihara, K.; Kondo, S.; Yamamoto, H. Synlett 2001, 1391.
48. Review: Heaney H. Trost B.M., Fleming I., Comprehensive Organic Synthesis. Vol. 2:1991;733 Pergamon, Oxford.