Simple and Efficient Procedure for the Friedel–Crafts Acylation of Aromatic Compounds with Carboxylic Acids in the Presence of P₂O₅/AL₂O₃ Under Heterogeneous Conditions

REFERENCES

• Heaney , H. In Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon Press : Oxford , 1991 ; vol. 2 , p. 733 .
   Google Scholar
• (a) Olah , G. A. ; Malhotra , R. ; Narang , S. C. ; Olah , J. A. Heterogenous catalysis by solid superacids, 11: Perfluorinated resinsulfonic acid (nafion-H)2 catalyzed friedel-crafts acylation of benzene and substituted benzenes . Synthesis 1978 , 672 ; (b) Kawada , A. ; Mitamura , S. ; Kobayashi , S. Scandium trifluoromethanesulfonate: A novel catalyst for Friedel–Crafts acylation . Synlett 1994 , 545 ; (c) Matsuo , J. ; Odashima , K. ; Kobayashi , S. Gallium nonafluorobutanesulfonate as an efficient catalyst in Friedel–Crafts acylation . Synlett 2000 , 403 ; (d) Effenberger , F. ; Buckel , F. ; Maier , A. H. ; Schmider , J. perfluoroalkanesulfonic acid catalyzed acylations of alkylbenzenes: synthesis of alkylanthraquinones . Synthesis 2000 , 1427 ; (e) Bartoli , G. ; Bosco , M. ; Marcantoni , E. ; Massaccesi , M. ; Rinaldi , S. ; Sambri , L. LiClO4–acyl anhydrides complexes as powerful acylating reagents of aromatic compounds in solvent free conditions . Tetrahedron Lett. 2002 , 43 , 6331 ; (f) Repichet , S. ; Roux , C. L. ; Roques , N. ; Dubac , J. BiCl3-catalyzed Friedel–Crafts acylation reactions: Bismuth(III) oxychloride as a water insensitive and recyclable procatalyst . Tetrahedron Lett. 2003 , 44 , 2037 ; (g) Firouzabadi , H. ; Iranpoor , N. ; Nowrouzi , F. Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel–Crafts acylation of aromatic compounds under solvent-less conditions . Tetrahedron 2004 , 60 , 10843 .
   Google Scholar
• (a) Chiche , B. ; Finiels , A. ; Gauthier , C. ; Geneste , P. Friedel–Crafts acylation of toluene and p-xylene with carboxylic acids catalyzed by zeolites . J. Org. Chem. 1986 , 51 , 2128 ; (b) Gauthier , C. ; Chiche , B. ; Finiels , A. ; Geneste , P. Influence of acidity in Friedel–Crafts acylation catalyzed by zeolites . J. Mol. Catal. 1989 , 50 , 219 ; (c) Wang , Q. L. ; Ma , Y. ; Ji , X. ; Yan , H. ; Qiu , Q. Regioselective acylation of anisole with carboxylic acids over HZSM-5 catalyst . J. Chem. Soc., Chem. Commun. 1995 , 2307 ; (d) Singh , A. P. ; Pandey , A. K. Acetylation of benzene to acetophenone over zeolite catalysts . J. Mol. Catal. A 1997 , 123 , 141 ; (e) Pandey , A. K. ; Singh , A. P. A novel catalytic method for the acylation of aromatics to the corresponding ketones over zeolite catalysts . Catal. Lett. 1997 , 44 , 129 ; (f) De Castro , C. ; Primo , J. ; Corma , A. Heteropolyacids and large-pore zeolites as catalysts in acylation reactions using α,β-unsaturated organic acids as acylating agents . J. Mol. Catal. A 1998 , 134 , 215 .
   Web of Science ®Google Scholar
• (a) Izumi , Y. ; Ogawa , M. ; Nohara , W. ; Urabe , K. Acidic alkali metal salts and ammonium salts of Keggin-type heteropolyacids as efficient solid acid catalysts for liquid-phase Friedel–Crafts reactions . Chem. Lett. 1992 , 1987 ; (b) Kaur , J. ; Kozhevnikov , I. V. Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalysed by heteropoly salt Cs2.5H0.5PW12O40 . Chem. Commun. 2002 , 2508 ; (c) Firouzabadi , H. ; Iranpoor , N. ; Nowrouzi , F. Solvent-free Friedel–Crafts acylation of aromatic compounds with carboxylic acids in the presence of trifluoroacetic anhydride and aluminum dodecatungstophosphate . Tetrahedron Lett. 2003 , 44 , 5343 .
   Web of Science ®Google Scholar
• Chiche , B. ; Finiels , A. ; Gautheir , C. ; Geneste , P. Acylation over cation-exchanged montmorillonite . J. Mol. Catal. 1987 , 42 , 229 .
   Google Scholar
• Ranu , B. C. ; Ghosh , K. ; Jana , U. Simple and improved procedure for regioselective acylation of aromatic ethers with carboxylic acids on the solid surface of alumina in the presence of trifluoroacetic anhydride . J. Org. Chem. 1996 , 61 , 9546 .
   Web of Science ®Google Scholar
• Sarvari , M. H. ; Sharghi , H. Simple and improved procedure for the regioselective acylation of aromatic ethers with carboxylic acids on the surface of graphite in the presence of methanesulfonic acid . Synthesis 2004 , 2165 .
   Google Scholar
• (a) Suzuki , K. ; Kitagawa , H. ; Mukaiyama , T. The catalytic Friedel–Crafts acylation reaction starting from aromatic compounds and free carboxylic acids (or their trimethylsilyl esters) by promotion of silicon(IV) cationic species via mixed anhydrides. Bull . Chem. Soc. Jpn. 1993 , 66 , 3729 ; (b) Kobayashi , S. ; Moriwaki , M. ; Hachiya , I. Catalytic direct C-acylation of phenol and naphthol derivatives using carboxylic acids as acylating reagents . Tetrahedron Lett. 1996 , 37 , 4183 ; (c) Kawamura , M. ; Cui , D. M. ; Hayashi , T. ; Shimada , S. Lewis acid–catalyzed Friedel–Crafts acylation reaction using carboxylic acids as acylating agents . Tetrahedron Lett. 2003 , 44 , 7715 .
   Google Scholar
• (a) Polshettiwar , V. ; Kaushik , M. P. A new, efficient, and simple method for the thionation of ketones to thioketones using P4S10/Al2O3 . Tetrahedron Lett. 2004 , 45 , 6255 ; (b) Blass , B. E. KF/Al2O3-mediated organic synthesis . Tetrahedron 2002 , 58 , 9301 .
   Web of Science ®Google Scholar
• (a) March , J. Advanced Organic Chemistry, , 3rd ed. ; John Wiley : New York , 1985 ; p. 904 ; (b) Eaton, P. E.; Carlson, G. R.; Lee, J. T. Phosphorus pentoxide–methanesulfonic acid: Convenient alternative to polyphosphoric acid. J. Org. Chem. 1973, 38, 4071; (c) Eshghi, H.; Rafei, M.; Karimi, M. H. P2O5/SiO2 as an efficient reagent for esterification of phenols in dry media. Synth. Commun. 2001, 31, 771.
   Google Scholar
• (a) Hajipour , A. R. ; Zarei , A. ; Khazdooz , L. ; Pourmousavi , S. A. ; Mirjalilli , F. ; Ruoho , A. E. Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid using supported P2O5/Al2O3 . Phosphorus, Sulfur Silicon Relat. Elem. 2005 , 180 , 2029 ; (b) Hajipour , A. R. ; Zarei , A. ; Ruoho , A. E. P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 2881 . (c) Naeimi , H. ; Salimi , F. ; Rabiei , K. Mild and convenient one-pot synthesis of Schiff bases in the presence of P2O5/Al2O3 as new catalyst under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 260 , 100 .
   Web of Science ®Google Scholar
• Clark , J. H. Catalysis of Organic Supported Inorganic Reagents ; VCH : New York , 1994 ; p. 2 .
   Google Scholar