SbCl₃ as a Highly Efficient Catalyst for the Acetylation of Alcohols, Phenols, and Amines under Solvent‐Free Conditions

References

• Greene , T. W. and Wuts , P. G. M. 1999 . Protective Groups in Organic Synthesis , 3rd edn. Vol. 149 , 373 New York : John Wiley & Sons .
   Google Scholar
• Zhdanov , R. I. and Zhenodarova , S. M. 1975 . Chemical methods of oligonucleotide synthesis . Synthesis , : 222
   Web of Science ®Google Scholar
• Stork , G. , Takahashi , T. , Kawamoto , I. and Suzuki , T. 1978 . Total synthesis of prostaglandin F2α by chirality transfer from D ‐glucose . J. Am. Chem. Soc. , 100 : 8272
   Web of Science ®Google Scholar
• Dauban , W. G. , Bune , R. A. , Gerdes , J. M. , Henger , K. E. , Cunningham , A. F. Jr. and Ottoboni , T. B. 1983 . Organic reactions at high pressure. A mild method for the placement of protecting groups on hindered and sensitive alcohols . Tetrahedron Lett. , 24 : 5709
   Google Scholar
• Horton , D. 1973 . Organic Syntheses Vol. V , 1 New York : Wiley . coll
   Google Scholar
• Hofle , G. , Steglich , V. and Vogruggen , H. 1978 . 4‐Dialkylaminopyridines as highly active acylation catalysts . Angew. Chem., Int. Ed. Engl. , 17 : 569
   Web of Science ®Google Scholar
• Scriven , E. F. V. 1983 . 4‐Dialkylaminopyridines: Super acylation and alkylation catalysts . Chem. Soc. Rev. , 12 : 129
   Web of Science ®Google Scholar
• Hirose , T. , Kopek , B. G. , Wang , Z. H. , Yusa , R. and Baldwin , B. W. 2003 . Microwave oven synthesis of esters promoted by imidazole . Tetrahedron Lett. , 44 : 1831
   Google Scholar
• Paul , S. , Nanda , P. , Gupta , R. and Loupy , A. 2002 . Ac2O–Py/basic alumina as a versatile reagent for acetylations in solvent‐free conditions under microwave irradiation . Tetrahedron Lett. , 43 : 4261
   Web of Science ®Google Scholar
• Vedejs , E. and Diver , S. T. 1993 . Tributylphosphine: A remarkable acylation catalyst . J. Am. Chem. Soc. , 115 : 3358
   Web of Science ®Google Scholar
• Vedejs , E. , Bennett , N. S. , Conn , L. M. , Diver , S. T. , Gingaves , M. , Lin , S. , Oliver , P. A. and Peterson , M. J. 1993 . Tributylphosphine‐catalyzed acylations of alcohols . J. Org. Chem. , 58 : 7286
   Web of Science ®Google Scholar
• Ishihara , K. , Kuboto , M. , Kurihara , H. and Yamamoto , H. 1995 . Scandium trifluoromethanesulfonate as an extremely active acylation catalyst . J. Am. Chem. Soc. , 117 : 4413
   Web of Science ®Google Scholar
• Ishihara , K. , Kubota , M. and Yamamoto , H. 1996 . A new scandium complex as an extremely active acylation catalyst . Synlett , : 265
   Google Scholar
• Iqbal , J. and Srivastava , R. R. 1992 . Cobalt (II) chloride catalyzed acylation of alcohols with acetic anhydride: Scope and mechanism . J. Org. Chem. , 57 : 2001
   Web of Science ®Google Scholar
• Yadav , J. S. , Narsaiah , A. V. , Basak , A. K. , Goud , P. R. , Sreenu , D. and Nagaiah , K. 2006 . Niobium pentachloride: An efficient catalyst for the selective acetylation of amines and thiols under mild conditions . J. Mol. Catal. A: Chem. , 255 : 78
   Web of Science ®Google Scholar
• Chauhan , K. K. , Frost , C. G. , Love , I. and Waite , D. 1999 . Indium triflate: An efficient catalyst for acylation reactions . Synlett , : 1743
   Web of Science ®Google Scholar
• Procopiou , P. A. , Baugh , S. P. D. , Flack , S. S. and Inglis , G. G. A. 1996 . An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst . Chem. Commun. , : 2625
   Google Scholar
• Procopiou , P. A. , Baugh , S. P. D. , Flack , S. S. and Inglis , G. G. A. 1998 . An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate . J. Org. Chem. , 63 : 2342
   Web of Science ®Google Scholar
• Chandrasekhar , S. , Ramachander , T. and Takhi , M. 1998 . Acylation of alcohols with acetic anhydride catalyzed by TaCl5: Some implications in kinetic resolution . Tetrahedron Lett. , 39 : 3263
   Web of Science ®Google Scholar
• Chandra , K. L. , Saravanan , P. , Singh , R. K. and Singh , V. K. 2002 . Lewis acid catalyzed acylation reactions: Scope and limitations . Tetrahedron , 58 : 1369
   Web of Science ®Google Scholar
• Saravanan , P. and Singh , V. K. 1999 . An efficient method for acylation reactions . Tetrahedron Lett. , 40 : 2611
   Web of Science ®Google Scholar
• Mohammad Poor Boltark , I. , Aliyan , H. and Khosropour , A. K. 2001 . Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols . Tetrahedron , 57 : 5851
   Google Scholar
• Dalpozzo , R. , De Nino , A. , Maiuolo , L. , Procopio , A. , Nardi , M. , Bartoli , G. and Romeo , R. 2003 . Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate . Tetrahedron Lett. , 44 : 5621
   Web of Science ®Google Scholar
• Karimi , B. and Maleki , J. 2003 . Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions . J. Org. Chem. , 68 : 4951
   PubMed Web of Science ®Google Scholar
• Ballini , R. , Bosica , G. , Carloni , S. , Ciaralli , L. , Maggi , R. and Sartori , G. 1998 . Zeolite HSZ‐360 as a new reusable catalyst for the direct acetylation of alcohols and phenols under solventless conditions . Tetrahedron Lett. , 39 : 6049
   Web of Science ®Google Scholar
• Bhaskar , P. M. and Loganathan , D. 1998 . Per‐O‐acetylation of sugars catalysed by montmorillonite K‐10 . Tetrahedron Lett. , 39 : 2215
   Web of Science ®Google Scholar
• Li , A.‐X. , Li , T.‐S. and Ding , T.‐H. 1997 . Montmorillonite K‐10 and KSF as remarkable acetylation catalysts . Chem. Commun. , : 1389
   Web of Science ®Google Scholar
• Kumareswaran , R. , Pachamuthu , K. and Vankar , Y. D. 2000 . Nafion‐H catalyzed acetylation of alcohols . Synlett , : 1652
   Google Scholar
• Kumar , P. , Pandey , R. K. , Bodas , M. S. and Dongare , M. K. 2001 . Yttria‐zirconia‐based Lewis acid: An efficient and chemoselective catalyst for acylation reactions . Synlett , : 206
   Google Scholar
• Nakae , Y. , Kusaki , I. and Sato , T. 2001 . Lithium‐perchlorate‐catalyzed acetylation of alcohols under mild reaction conditions . Synlett , : 1584
   Google Scholar
• Bartoli , G. , Bosco , M. , Dalpozzo , R. , Marcantoni , E. , Massaccesi , M. , Rinaldi , S. and Sambri , L. 2003 . Mg(ClO4)2 as a powerful catalyst for the acylation of alcohols under solvent‐free conditions . Synlett , : 39
   Web of Science ®Google Scholar
• Chakraborti , A. K. and Shivani . 2006 . Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst . J. Org. Chem. , 71 : 5785
   PubMed Web of Science ®Google Scholar
• Chakraborti , A. K. and Gulhane , R. 2003 . Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines . Tetrahedron Lett. , 44 : 6749
   Web of Science ®Google Scholar
• Forsyth , S. A. , MacFarlane , D. R. , Thomson , R. J. and von Itzstein , M. 2002 . Rapid, clean, and mild O‐acetylation of alcohols and carbohydrates in an ionic liquid . Chem. Commun. , : 714
   Google Scholar
• Lee , S.‐G. and Park , J. H. 2003 . Metallic Lewis acids–catalyzed acetylation of alcohols with acetic anhydride and acetic acid in ionic liquids: Study on reactivity and reusability of the catalysts . J. Mol. Catal. A: Chem. , 194 : 49
   Web of Science ®Google Scholar
• Srikanth , R. T. , Narasimhulu , M. , Suryakiran , N. , Chinni , M. K. , Ashalatha , K. and Venkateswarlu , Y. 2006 . A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3 · 6H2O as a catalyst under solvent‐free conditions . Tetrahedron Lett. , 47 : 6825
   Google Scholar
• Phukan , P. 2004 . Iodine as an extremely powerful catalyst for the acetylation of alcohols under solvent‐free conditions . Tetrahedron Lett. , 45 : 4785
   Web of Science ®Google Scholar
• Chakraborti , A. K. , Gulhane , R. and Shivani . 2004 . Copper(II) tetrafluoroborate–catalyzed acetylation of phenols, thiols, alcohols, and amines . Synthesis , : 111 and references cited therein
   Google Scholar
• Sweet , D. V. 1988 . Registry of Toxic Effects of Chemical Substances 1985–86 3336 Washington D.C. : U.S. Government Printing Office .
   Google Scholar
• Sweet , D. V. 1988 . Registry of Toxic Effects of Chemical Substances 1985–86 4049 Washington D.C. : U.S. Government Printing Office .
   Google Scholar
• Buckler , S. A. 1962 . Autoxidation of trialkylphosphines . J. Am. Chem. Soc. , 84 : 3093
   Web of Science ®Google Scholar
• Bhattacharya , A. K. and Kaur , T. 2007 . An efficient one‐pot synthesis of α‐amino phosphonates catalyzed by bismuth nitrate pentahydrate . Synlett , : 745
   Google Scholar
• Bhattacharya , A. K. and Rana , K. C. 2007 . Microwave‐assisted synthesis of 14‐aryl‐14H‐dibenzo[a.j]xanthenes catalysed by methanesulfonic acid under solvent‐free conditions . Mendeleev Commun. , 17 : 247
   Web of Science ®Google Scholar
• Bhattacharya , A. K. , Mujahid , M. and Natu , A. A. 2008 . An efficient method for the synthesis of acylals from aldehydes under solvent‐free conditions catalyzed by antimony trichloride . Synth. Commun. , 38 : 128 – 134 .
   Web of Science ®Google Scholar
• Bhattacharya , A. K. and Rana , K. C. 2008 . Amberlite‐IR 120 catalyzed three‐component synthesis of α‐amino phosphonates in one‐pot . Tetrahedron Lett. , 49 [doi:10.1016/j.tetlet.2008.02.102]
   Google Scholar
• Mazières , S. , Roux , C. L. , Peyronneau , M. , Gornitzka , H. and Roques , N. 2004 . Eur. J. Inorg. Chem. , : 2823
   Web of Science ®Google Scholar
• Francom , P. , Janeba , Z. , Shibuya , S. and Robis , M. 2002 . Nucleic acid related compounds, 116: Nonaqueous diazotization of aminopurine nucleosides: Mechanistic considerations and efficient procedures with tert‐butyl nitrite or sodium nitrite . J. Org. Chem. , 67 : 6788
   PubMed Web of Science ®Google Scholar
• Lal , G. S. , Lobach , E. and Evans , A. 2000 . Fluorination of thiocarbonyl compounds with bis(2‐methoxyethyl)aminosulfur trifluoride (deoxo‐fluor reagent): A facile synthesis of gem‐difluorides . J. Org. Chem. , 65 : 4830
   PubMed Web of Science ®Google Scholar
• Maiti , G. and Kundu , P. 2006 . Imino Diels–Alder reactions: An efficient one‐pot synthesis of pyrano and furanoquinoline derivatives catalyzed by SbCl3 . Tetrahedron Lett. , 47 : 5733
   Web of Science ®Google Scholar