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Volumn 15, Issue 7, 2012, Pages 576-579

Pentafluorophenylammonium triflate as a mild and new organocatalyst for acylation of alcohols, phenols, and amines under solvent-free condition

Author keywords

Alcohols; Organocatalyst; Pentafluorophenylammonium triflate; Phenol

Indexed keywords

PENTAFLUOROPHENYLAMMONIUM TRIFLATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 84865371619     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/138620712801619203     Document Type: Article
Times cited : (5)

References (29)
  • 1
    • 0026591449 scopus 로고
    • A facile conversion of halides, alcohols and olefins to esters using iron(III) perchlorate
    • 2O catalytic esterification of aliphatic carboxylic acids with alcohols. Synth. Commun., 1998, 28, 1159. (c) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; John Wiley & Sons: New York, 1999, 1955. (d) Otera, J. Esterification; Wiley-VCH: Weinheim, 2003. (e) Greene, T. W.; Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons: New Jersey, 2007, 223.
    • 2O catalytic esterification of aliphatic carboxylic acids with alcohols. Synth. Commun., 1998, 28, 1159. (c) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; John Wiley & Sons: New York, 1999, 1955. (d) Otera, J. Esterification; Wiley-VCH: Weinheim, 2003. (e) Greene, T. W.; Wuts, P. G. M. Greene's Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons: New Jersey, 2007, 223.
    • (1992) Synth. Commun. , vol.22 , pp. 1087-1094
    • Kumar, B.1    Kumar, H.2    Parmar, A.3
  • 2
    • 84981783095 scopus 로고
    • N-dimethyl-4-pyridinamine, a very effective acylation catalyst
    • Steglich, W.; Höfle, G. N,N-Dimethyl-4-pyridinamine, a very effective acylation catalyst. Angew. Chem., Int. Ed., 1969, 8, 981.
    • (1969) Angew. Chem., Int. Ed. , vol.8 , pp. 981
    • Steglich, W.1    Höfle, G.N.2
  • 4
    • 33751391774 scopus 로고
    • Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: Scope and mechanism
    • Iqbal, J.; Srivastava, R. R. Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism. J. Org. Chem., 1992, 57, 2001-2007.
    • (1992) J. Org. Chem. , vol.57 , pp. 2001-2007
    • Iqbal, J.1    Srivastava, R.R.2
  • 5
    • 0002563662 scopus 로고
    • Transesterification catalyzed by lanthanoid tri-2-propoxides
    • Okano, T.; Miyamoto, K.; Kiji, J. Transesterification catalyzed by lanthanoid tri-2-propoxides. Chem. Lett., 1995, 246.
    • (1995) Chem. Lett. , vol.246
    • Okano, T.1    Miyamoto, K.2    Kiji, J.3
  • 6
    • 17844380747 scopus 로고    scopus 로고
    • Gadolinium triflate immobilized in imidazolium based ionic liquids: A recyclable catalyst and green solvent for acetylation of alcohols and amines
    • (a)
    • (a) Alleti, R.; Oh, W. S.; Perambuduru, M.; Afrasiabi, Z.; Sinn, E.; Reddy, V. P. Gadolinium triflate immobilized in imidazolium based ionic liquids: a recyclable catalyst and green solvent for acetylation of alcohols and amines. Green Chem., 2005, 7, 203. (b) Alleti, R.; Perambuduru, M.; Samantha, S.; Reddy, V. P. Gadolinium triflate: an efficient and convenient catalyst for acetylation of alcohols and amines. J. Mol. Catal. A: Chem., 2005, 226, 57-59.
    • (2005) Green Chem. , vol.7 , pp. 203
    • Alleti, R.1    Oh, W.S.2    Perambuduru, M.3    Afrasiabi, Z.4    Sinn, E.5    Reddy, V.P.6
  • 7
    • 0032516319 scopus 로고    scopus 로고
    • 5: Some implications in kinetic resolution
    • DOI 10.1016/S0040-4039(98)00465-1, PII S0040403998004651
    • Chandrasekhar, S.; Ramachander, T.; Takhi, M. Acylation of alcohols with acetic anhydride catalyzed by TaCl5: Some implications in kinetic resolution. Tetrahedron Lett., 1998, 39, 3263-3266. (Pubitemid 28198005)
    • (1998) Tetrahedron Letters , vol.39 , Issue.20 , pp. 3263-3266
    • Chandrasekhar, S.1    Ramachander, T.2    Takhi, M.3
  • 8
    • 0032753189 scopus 로고    scopus 로고
    • Indium triflate: An efficient catalyst for acylation reactions
    • Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Indium triflate: an efficient catalyst for acylation reactions. Synlett., 1999, 1743-1744. (Pubitemid 29529435)
    • (1999) Synlett , Issue.11 , pp. 1743-1744
    • Chauhan, K.K.1    Frost, C.G.2    Love, I.3    Waite, D.4
  • 9
    • 0033605890 scopus 로고    scopus 로고
    • An efficient method for acylation reactions
    • DOI 10.1016/S0040-4039(99)00229-4, PII S0040403999002294
    • Saravanan, P.; Singh, V. K. An efficient method for acylation reactions. Tetrahedron Lett., 1999, 40, 2611-2614. (Pubitemid 29130545)
    • (1999) Tetrahedron Letters , vol.40 , Issue.13 , pp. 2611-2614
    • Saravanan, P.1    Singh, V.K.2
  • 10
    • 0034683052 scopus 로고    scopus 로고
    • 3 as catalyst
    • DOI 10.1002/1521-3773 (20000818) 39:16<2877::AID-ANIE2877>3.0.CO;2- V
    • Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. Highly efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst. Angew. Chem., Int. Ed. Eng., 2000, 39, 2877-2879. (Pubitemid 30663809)
    • (2000) Angewandte Chemie - International Edition , vol.39 , Issue.16 , pp. 2877-2879
    • Orita, A.1    Tanahashi, C.2    Kakuda, A.3    Otera, J.4
  • 11
    • 0003002340 scopus 로고    scopus 로고
    • Montmorillonite K-10 and KSF as remarkable acetylation catalysts
    • Li, A.-I.; Li, T.-S.; Ding, T.-H. Montmorillonite K-10 and KSF as remarkable acetylation catalysts. Chem. Commun., 1997, 1389-1390. (Pubitemid 127496043)
    • (1997) Chemical Communications , Issue.15 , pp. 1389-1390
    • Li, A.-X.1    Li, T.-S.2    Ding, T.-H.3
  • 12
  • 13
    • 58649091794 scopus 로고    scopus 로고
    • O-benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: Advantages and limitations
    • Barbero, M.; Cadamuro, S.; Dughera, S.; Venturello, P. o-Benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: advantages and limitations. Synthesis, 2008, 3625-3632.
    • (2008) Synthesis , pp. 3625-3632
    • Barbero, M.1    Cadamuro, S.2    Dughera, S.3    Venturello, P.4
  • 14
    • 1642359808 scopus 로고    scopus 로고
    • Zirconiuni(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions
    • Chakraborti, A.K.; Gulhane, R. Zirconium(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions. Synlett., 2004, 4, 627-630. (Pubitemid 38388783)
    • (2004) Synlett , Issue.4 , pp. 627-630
    • Chakraborti, A.K.1    Gulhane, R.2
  • 15
    • 33746335364 scopus 로고    scopus 로고
    • Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst
    • DOI 10.1021/jo0605142
    • Chakraborti, A. K.; Shivani. Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst. J. Org. Chem., 2006, 71, 5785-5788. (Pubitemid 44117032)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.15 , pp. 5785-5788
    • Chakraborti, A.K.1    Shivani2
  • 16
    • 0041669215 scopus 로고    scopus 로고
    • Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines
    • DOI 10.1016/S0040-4039(03)01641-1
    • Chakraborti, A. K.; Gulhane, R. Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines. Tetrahedron Lett., 2003, 44, 6749-6753. (Pubitemid 36945129)
    • (2003) Tetrahedron Letters , vol.44 , Issue.35 , pp. 6749-6753
    • Chakraborti, A.K.1    Gulhane, R.2
  • 17
    • 0347949538 scopus 로고    scopus 로고
    • Copper(II) tetrafluoroborate-catalyzed acetylation of phenols, thiols, alcohols, and amines
    • Chakraborti, A. K.; Gulhane, R.; Shivani. Copper(II) tetrafluoroborate- catalyzed acetylation of phenols, thiols, alcohols, and amines. Synthesis, 2004, 111-115. (Pubitemid 38067772)
    • (2004) Synthesis , Issue.1 , pp. 111-115
    • Chakraborti, A.K.1    Gulhane, R.2    Shivani3
  • 18
    • 0142028665 scopus 로고    scopus 로고
    • Bismuth oxide perchlorate as a highly efficient catalyst for heteroatom acylation under solvent-free conditions
    • Chakraborti, A. K.; Gulhane, R.; Shivani, S. Bismuth oxide perchlorate as a highly efficient catalyst for heteroatom acylation under solvent-free conditions. Synlett., 2003, 1805.
    • (2003) Synlett. , vol.1805
    • Chakraborti, A.K.1    Gulhane, R.2    Shivani, S.3
  • 19
    • 0037459871 scopus 로고    scopus 로고
    • Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines
    • DOI 10.1016/S0040-4039(03)00683-X
    • Chakraborti, A. K.; Gulhane, R. Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines. Tetrahedron Lett., 2003, 44, 3521-3525. (Pubitemid 36398325)
    • (2003) Tetrahedron Letters , vol.44 , Issue.17 , pp. 3521-3525
    • Chakraborti, A.K.1    Gulhane, R.2
  • 21
    • 33847184270 scopus 로고    scopus 로고
    • 2O] as acylation catalyst for poor nucleophilic phenols, alcohols and amines: Scope and limitations
    • DOI 10.1016/j.molcata.2006.09.015, PII S1381116906012180
    • 2O] as acylation catalyst for poor nucleophilic phenols, alcohols and amines: scope and limitations. J. Mol. Catal. A, 2007, 264, 208-213. (Pubitemid 46329584)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.264 , Issue.1-2 , pp. 208-213
    • Shivani1    Gulhane, R.2    Chakraborti, A.K.3
  • 22
    • 0041666708 scopus 로고    scopus 로고
    • Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines
    • Chakraborti, A. K.; Gulhane, R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun., 2003, 1896-1897. (Pubitemid 36920752)
    • (2003) Chemical Communications , Issue.15 , pp. 1896-1897
    • Chakraborti, A.K.1    Gulhane, R.2
  • 23
    • 0012615648 scopus 로고    scopus 로고
    • Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides
    • Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. Scandium trifluoromethanesulfonate as an extremely active lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides. J. Org. Chem., 1996, 61, 4560-4567. (Pubitemid 126523465)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.14 , pp. 4560-4567
    • Ishihara, K.1    Kubota, M.2    Kurihara, H.3    Yamamoto, H.4
  • 24
    • 85011245852 scopus 로고
    • Scandium trifluoromethanesulfonate as an extremely active acylation catalyst
    • Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. Scandium trifluoromethanesulfonate as an extremely active acylation catalyst. J. Am. Chem. Soc., 1995, 117, 4413-4414.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4413-4414
    • Ishihara, K.1    Kubota, M.2    Kurihara, H.3    Yamamoto, H.4
  • 25
    • 74549215797 scopus 로고    scopus 로고
    • Solvent-free iron(III) chloride catalyzed O- S- and N-acylation under mild conditions
    • Mihara, M.; Nakai, T.; Iwai T.; Ito, T.; Ohno T.; Mizuno, T. Solvent-free iron(III) chloride catalyzed O-, S-, and N-acylation under mild conditions. Synlett., 2010, 253-255.
    • (2010) Synlett , pp. 253-255
    • Mihara, M.1    Nakai, T.2    Iwai, T.3    Ito, T.4    Ohno, T.5    Mizuno, T.6
  • 26
    • 34948892808 scopus 로고    scopus 로고
    • Trimethylsilyl trifluoromethanesulfonate as a metal-free, homogeneous and strong lewis acid catalyst for efficient one-pot synthesis of alpha-aminonitriles and their fluorinated analogues
    • DOI 10.1055/s-2007-985594
    • Prakash, G. K. S.; Panja, C.; Do, C.; Mathew, T.; Olah, G. A. Trimethylsilyl trifluoromethanesulfonate as a metal-free, homogeneous and strong Lewis acid catalyst for efficient one-pot synthesis of α-aminonitriles and their fluorinated analogues. Synlett., 2007, 2395-2399. (Pubitemid 47522003)
    • (2007) Synlett , Issue.15 , pp. 2395-2399
    • Prakash, G.K.S.1    Panja, C.2    Do, C.3    Mathew, T.4    Olah, G.A.5
  • 27
    • 79959505940 scopus 로고    scopus 로고
    • Organocatalytic enantioselective acyl transfer onto racemic as well as meso alcohols, amines, and thiols
    • A review
    • A review: Christian E. Müller, C. E.; Schreiner, P. R. Organocatalytic enantioselective acyl transfer onto racemic as well as meso alcohols, amines, and thiols. Angew. Chem. Int. Ed., 2011, 50, 6012-6042.
    • (2011) Angew. Chem. Int. Ed. , Issue.50 , pp. 6012-6042
    • Christian, E.1    Müller, C.E.2    Schreiner, P.R.3
  • 28
    • 33751359795 scopus 로고    scopus 로고
    • Pentafluorophenylammonium triflate (PFPAT): An efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation
    • DOI 10.1039/b609181b
    • Commercially available; TCI Product No- P1626: a) Funatomi, T.; Wakasugi, K.; Misaki, T.; Tanabe, Y. Pentafluorophenylammonium triflate (PFPAT): an efficient, practical, and cost-effective catalyst for esterification, thioesterification, transesterification, and macrolactone formation. Green Chem., 2006, 8, 1022-1027; b) Iida, A.; Osada, J.; Nagase, R.; Misaki, T.; Tanabe, Y. Mild and efficient pentafluorophenylammonium triflate (PFPAT)-catalyzed Cacylations of enol silyl ethers or ketene silyl (thio)acetals with acid chlorides. Org. Lett., 2007, 9, 1859-1862. (Pubitemid 44813945)
    • (2006) Green Chemistry , vol.8 , Issue.12 , pp. 1022-1027
    • Funatomi, T.1    Wakasugi, K.2    Misaki, T.3    Tanabe, Y.4
  • 29
    • 79958784352 scopus 로고    scopus 로고
    • Pentafluorophenylammonium triflate (PFPAT): An efficient, metal-free and reusable catalyst for the von Pechmann reaction
    • (a) (b) Khaksar, Ostad, S. M. Pentafluorophenylammonium triflate as an efficient, environmentally friendly and novel organocatalyst for synthesis of bis-indolyl methane derivatives. J. Fluorine. Chem., 2011, 132, 937-939
    • (a) Montazeri, N.; Khaksar, S.; Nazari, A.; Alavi, S. S.; Vahdat, S. M.; Tajbakhsh, M. Pentafluorophenylammonium triflate (PFPAT): An efficient, metal-free and reusable catalyst for the von Pechmann reaction. J. Fluorine. Chem., 2011, 132, 450-452; (b) Khaksar, Ostad, S. M. Pentafluorophenylammonium triflate as an efficient, environmentally friendly and novel organocatalyst for synthesis of bis-indolyl methane derivatives. J. Fluorine. Chem., 2011, 132, 937-939.
    • (2011) J. Fluorine. Chem. , vol.132 , pp. 450-452
    • Montazeri, N.1    Khaksar, S.2    Nazari, A.3    Alavi, S.S.4    Vahdat, S.M.5    Tajbakhsh, M.6


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