A novel and simple method for the silylation of alcohols in DMSO-hexane without a catalyst

Green Chemistry

Volumn 5, Issue 1, 2003, Pages 82-84

  Watahiki, Tsutomu ^a   Matsuzaki, Masaya ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; CHLORIDE; CYCLOPROPANE; DIMETHYL SULFOXIDE; ETHER DERIVATIVE; HEXANE; TERT BUTYLDIMETHYLSILYL CHLORIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; ROOM TEMPERATURE; SILYLATION; TEMPERATURE SENSITIVITY;

EID: 0141603738     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209506h     Document Type: Article

References (18)

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7. G. A. Olah, B. G. B. Gupta, S. C. Narang and R. Malhotra, J. Org. Chem., 1979, 44, 4272; G. R. Martinez, P. A. Grieco, E. Williams, K. Kanai and C. V. Srinivasan, J. Am. Chem. Soc., 1982, 104, 1436; J. M. Aizpurua and C. Palomo, Tetrahedron Lett., 1985, 26, 475; S. Kim and H. Chang, Bull. Chem. Soc. Jpn., 1985, 58, 3669; B. A. D'Sa, D. Mcleod and J. G. Verkade, J. Org. Chem., 1997, 62, 5057.
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9. G. A. Olah, B. G. B. Gupta, S. C. Narang and R. Malhotra, J. Org. Chem., 1979, 44, 4272; G. R. Martinez, P. A. Grieco, E. Williams, K. Kanai and C. V. Srinivasan, J. Am. Chem. Soc., 1982, 104, 1436; J. M. Aizpurua and C. Palomo, Tetrahedron Lett., 1985, 26, 475; S. Kim and H. Chang, Bull. Chem. Soc. Jpn., 1985, 58, 3669; B. A. D'Sa, D. Mcleod and J. G. Verkade, J. Org. Chem., 1997, 62, 5057.
10. G. A. Olah, B. G. B. Gupta, S. C. Narang and R. Malhotra, J. Org. Chem., 1979, 44, 4272; G. R. Martinez, P. A. Grieco, E. Williams, K. Kanai and C. V. Srinivasan, J. Am. Chem. Soc., 1982, 104, 1436; J. M. Aizpurua and C. Palomo, Tetrahedron Lett., 1985, 26, 475; S. Kim and H. Chang, Bull. Chem. Soc. Jpn., 1985, 58, 3669; B. A. D'Sa, D. Mcleod and J. G. Verkade, J. Org. Chem., 1997, 62, 5057.
11. 6 Allylsilane and silyl enol ether could also silylate alcohols under the influence of a catalytic amount of p-toluenesulfonic acid, trifluoromethanesulfonic acid or iodine. These methods do not need a work-up process, such as an extraction: T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 1980, 21, 835; T. Veysoglu and L. A. Mitscher, Tetrahedron Lett., 1981, 22, 1299; G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem and S. C. Narang, J. Org. Chem., 1981, 46, 5212; A. Hosomi and H. Sakurai, Chem. Lett., 1981, 85; T. Suzuki, T. Watahiki and T. Oriyama, Tetrahedron Lett., 2000, 41, 8903.
12. Allylsilane and silyl enol ether could also silylate alcohols under the influence of a catalytic amount of p-toluenesulfonic acid, trifluoromethanesulfonic acid or iodine. These methods do not need a work-up process, such as an extraction: T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 1980, 21, 835; T. Veysoglu and L. A. Mitscher, Tetrahedron Lett., 1981, 22, 1299; G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem and S. C. Narang, J. Org. Chem., 1981, 46, 5212; A. Hosomi and H. Sakurai, Chem. Lett., 1981, 85; T. Suzuki, T. Watahiki and T. Oriyama, Tetrahedron Lett., 2000, 41, 8903.
13. Allylsilane and silyl enol ether could also silylate alcohols under the influence of a catalytic amount of p-toluenesulfonic acid, trifluoromethanesulfonic acid or iodine. These methods do not need a work-up process, such as an extraction: T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 1980, 21, 835; T. Veysoglu and L. A. Mitscher, Tetrahedron Lett., 1981, 22, 1299; G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem and S. C. Narang, J. Org. Chem., 1981, 46, 5212; A. Hosomi and H. Sakurai, Chem. Lett., 1981, 85; T. Suzuki, T. Watahiki and T. Oriyama, Tetrahedron Lett., 2000, 41, 8903.
14. Allylsilane and silyl enol ether could also silylate alcohols under the influence of a catalytic amount of p-toluenesulfonic acid, trifluoromethanesulfonic acid or iodine. These methods do not need a work-up process, such as an extraction: T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 1980, 21, 835; T. Veysoglu and L. A. Mitscher, Tetrahedron Lett., 1981, 22, 1299; G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem and S. C. Narang, J. Org. Chem., 1981, 46, 5212; A. Hosomi and H. Sakurai, Chem. Lett., 1981, 85; T. Suzuki, T. Watahiki and T. Oriyama, Tetrahedron Lett., 2000, 41, 8903.
15. Allylsilane and silyl enol ether could also silylate alcohols under the influence of a catalytic amount of p-toluenesulfonic acid, trifluoromethanesulfonic acid or iodine. These methods do not need a work-up process, such as an extraction: T. Morita, Y. Okamoto and H. Sakurai, Tetrahedron Lett., 1980, 21, 835; T. Veysoglu and L. A. Mitscher, Tetrahedron Lett., 1981, 22, 1299; G. A. Olah, A. Husain, B. G. B. Gupta, G. F. Salem and S. C. Narang, J. Org. Chem., 1981, 46, 5212; A. Hosomi and H. Sakurai, Chem. Lett., 1981, 85; T. Suzuki, T. Watahiki and T. Oriyama, Tetrahedron Lett., 2000, 41, 8903.
16. 7 T. Oriyama, K. Kobayashi, T. Suzuki and M. Oda, Green Chem., 2002, 4, 30; K. Kobayashi, T. Watahiki and T. Oriyama, Synthesis, in press.
17. T. Oriyama, K. Kobayashi, T. Suzuki and M. Oda, Green Chem., 2002, 4, 30; K. Kobayashi, T. Watahiki and T. Oriyama, Synthesis, in press.
18. Y. Génisson and L. Gorrichon, Tetrahedron Lett., 2000, 41, 4881.