Pentafluorophenylammoniom Triflate
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 7 579
thiols, amines, and alcohols under solvent-free conditions. Synlett.,
[24]
[25]
[26]
Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. Scandium
trifluoromethanesulfonate as an extremely active acylation catalyst.
J. Am. Chem. Soc., 1995, 117, 4413-4414.
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.
2
004, 4, 627-630.
[
15]
16]
Chakraborti, A. K.; Shivani. Magnesium bistrifluoromethanesulfo-
nimide as a new and efficient acylation catalyst. J. Org. Chem.,
2
006, 71, 5785-5788.
[
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-
Prakash, G. K. S.; Panja, C.; Do, C.; Mathew, T.; Olah, G. A.
Trimethylsilyl trifluoromethanesulfonate as
a
metal-free,
6
753.
homogeneous and strong Lewis acid catalyst for efficient one-pot
synthesis of ꢁ-aminonitriles and their fluorinated analogues.
Synlett., 2007, 2395-2399.
A review: Christian E. Müller, C. E.; Schreiner, P. R. Organocatal-
ytic enantioselective acyl transfer onto racemic as well as meso
alcohols, amines, and thiols. Angew. Chem. Int. Ed., 2011, 50,
6012-6042.
Commercially available; TCI Product No- P1626: a) Funatomi, T.;
Wakasugi, K.; Misaki, T.; Tanabe, Y. Pentafluorophenylammon-
ium 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 C-
acylations of enol silyl ethers or ketene silyl (thio)acetals with acid
chlorides. Org. Lett., 2007, 9, 1859-1862.
(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.
[17]
[18]
[19]
[20]
[21]
Chakraborti, A. K.; Gulhane, R.; Shivani. Copper(II) tetrafluorobo-
rate-catalyzed acetylation of phenols, thiols, alcohols, and amines.
Synthesis, 2004, 111-115.
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.
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.
Chakraborti, A. K.; Sharma, L.; Gulhane Shivani, R. Electrostatic
catalysis by ionic aggregates: scope and limitations of Mg(ClO
as acylation catalyst. Tetrahedron, 2003, 59, 7661.
Shivani, R.; Gulhane, R.; Chakraborti, A.K. Zinc perchlorate
hexahydrate [Zn(ClO ꢀ6H O] as acylation catalyst for poor
[27]
[28]
4 2
)
4
)
2
2
nucleophilic phenols, alcohols and amines: scope and limitations. J.
Mol. Catal. A, 2007, 264, 208-213.
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,
[29]
[
22]
23]
1
896-1897.
[
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.
Received: June 3, 2011
Revised: November 24, 2011
Accepted: January 26, 2012