Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 17
920
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

New, Efficient, Selective, and One-Pot Method for Acylation of Amines

, , &
Pages 2929-2940 | Received 21 Oct 2007, Published online: 28 Aug 2008

REFERENCES

  • (a) Ahmad , S. ; Iqbal , J. Cobalt(II) chloride catalysed coupling of thiols and anhydrides: A new and efficient synthesis of thiol esters . Tetrahedron Lett . 1986 , 27 , 3791 – 3794 ; (b) Chandrashekhar, S.; Ramchander, T.; Takhi, M. Acylation of alcohols with acetic anhydride catalyzed by TaCl5: Some implications in kinetic resolution. Tetrahedron Lett. 1998, 39, 3263–3266; (c) 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; (d) De, S. K. Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines. Tetrahedron Lett. 2004, 45, 2919–2922 .
  • (a) Kamal , A. ; Khan , M. N. A. ; Reddy , K. S. ; Srikanth , Y. V. V. ; Krishnaji , T. Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions . Tetrahedron Lett . 2007 , 48 , 3813 – 3818 ; (b) 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; (c) Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3. J. Org. Chem. 2001, 66, 8926–8934; (d) Dalpozzo, R.; Nino, A. D.; Maiuolo, L.; Procopio, A.; Nardi, M.; Bartoli, G.; Romeo, R. Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate. Tetrahedron Lett. 2003, 44, 5621–5624; (e) Chauhan, K. K.; Frost, C. G.; Ian, L.; David W. Indium Triflate: An efficient catalyst for acylation reactions. Synlett. 1999, 1743–1744; (f) Chandra, K. L.; Sarvanan, P.; Singh, R. K.; Singh, V. K. Lewis acid catalyzed acylation reactions: scope and limitations. Tetrahedron 2002, 58, 1369–1374; (g) Procopiou, P. A.; Baugh S. P. D.; Flack, S. S.; Inglis, G. G. A. An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by Trimethylsilyl trifluoromethanesulfonate. J. Org. Chem. 1998, 63, 2342–2347; (h) Karimi, B.; Maleki, J. 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. 2003, 68, 4951–4954 .
  • (a) Nakae , Y. ; Kusaki , I. ; Sato , T. Lithium perchlorate catalyzed acetylation of alcohols under mild reaction conditions . Synlett . 2001 , 1584 – 1586 ; (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Mg(ClO4)2 as a powerful catalyst for the acylation of alcohols under solvent-free conditions. Synlett. 2003, 39–42; (c) Chakraborti, A. K.; Sharma, L.; Gulhane, R.; Shivani. Electrostatic catalysis by ionic aggregates: scope and limitations of Mg(ClO4)2 as acylation catalyst. Tetrahedron 2003, 59, 7661–7668; (d) Chakraborti, A. K.; Gulhane, R.; Shivani. Bismuth oxide perchlorate as a highly efficient catalyst for heteroatom acylation under solvent-free conditions. Synlett. 2003, 1805–1808 .
  • (a) 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 ; (b) 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; (c) Kumar, P.; Pandey, R. K.; Bodas, M. S.; Dongare, M. K. Yttria-Zirconia based lewis acid: an efficient and chemoselective catalyst for acylation reactions. Synlett. 2001, 206–209; (d) Billini, R.; Bosica,G.; Carloni, S.; Ciaralli, L.; Maggi, R.; Sartori G. Zeolite HSZ-360 as a new reusable catalyst for the direct acetylation of alcohols and phenols under solventless conditions. Tetrahedron Lett. 1998, 39, 6049–6052; (e) Li, A. X.; Li, T. S.; Ding, T. H. Montmorillonite K-10 and KSF as remarkable acetylation catalysts. Chem. Commun. 1997, 1389–1390; (f) Yadav, V. K.; Babu, K. G.; Mittal, M. KF–Al2O3 is an efficient solid support reagent for the acetylation of amines, alcohols, and phenols. Impeding effect of solvent on the reaction rate. Tetrahedron 2001, 57, 7047–7051 .
  • (a) Borah , R. ; Deka N. ; Sarma , J. C. J. Iodine as an acetyl transfer catalyst . J. Chem. Research (S) 1997 , 110 – 111 ; (b) Kartha, K. P. R.; Field, R. A. Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-acetylation, regioselective acylation and acetolysis. Tetrahedron 1997, 53, 11753–11766 .
  • Okano , T. ; Miyamoto , K. ; Kiji , J. Transesterification catalyzed by Lanthanoid tri-2-propoxides . Chem. Lett . 1995 , 24 , 246 – 246 .
  • Prasad , H. S. ; Srinivasa , G. R. ; Gowda , D. C. Convenient, Cost-effective, and mild method for the N-acetylation of anilines and secondary amines . Synth. Commun . 2005 , 35 , 1189 – 1195 .
  • Choudary , B. M. ; Kantam , M. L. ; Neeraja , V. ; Bandyopadhyay , T. ; Reddy , P. N. Vanadyl(IV) acetate, a new reusable catalyst for acetylation of alcohols . J. Mol. Cat. A 1999 , 140 , 25 – 29 .
  • Forsyth , S. A. ; MacFarlane , D. R. ; Thomson , R. J. ; Von Itzestein , M. Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid . Chem. Commun . 2002 , 714 – 715 .
  • Allevi , P. ; Ciuffreda , P. ; Longo , A. ; Anastasia , M. Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates. Tetrahedron: Asymmetry 1998, 9, 2915–2924.
  • Ghosh , R. ; Maiti , S. ; Chakraborty , A. Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl2 · 8H2O and acetyl chloride in solution and in solvent-free conditions . Tetrahedron Lett . 2005 , 46 , 147 – 151 .
  • Ghosh , R. ; Maiti , S. ; Chakraborty , A. Facile catalyzed acylation of heteroatoms using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride . Tetrahedron Lett . 2004 , 45 , 6775 – 6778 .
  • Iranpoor , N. ; Firouzabadi , H. ; Jamalian , A. Silphos [PCl3-n(SiO2)n]: a heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate . Tetrahedron Lett . 2005 , 46 , 7963 – 7966 .
  • Reddy , T. S. ; Narasimhulu , M. ; Suryakiran , N. ; Mahesh , K. C. ; Ashalatha , K. ; Venkateswarlu , Y. 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 . 2006 , 47 , 6825 – 6829 .
  • Ahmed , N. ; van Lier , J. E. Molecular iodine in isopropenyl acetate (IPA): a highly efficient catalyst for the acetylation of alcohols, amines and phenols under solvent free conditions . Tetrahedron Lett . 2006 , 47 , 5345 – 5349 .
  • Brar , A. ; Vankar , Y. D. A one-pot selective deprotective acetylation of benzyl ethers and OTBDMS ethers using the BF3 · Et2O–NaI–Ac2O reagent system . Tetrahedron Lett . 2006 , 47 , 5207 – 5210 .
  • Naik , S. ; Bhattacharjya , G. ; Talukdar , B. ; Patel , B. K. Chemoselective acylation of amines in aqueous Media . Eur. J. Org. Chem . 2004 , 1254 – 1260 .
  • (a) Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis, 3rd ed. ; John Wiley and Sons : New York , 1999 ; (b) Hanson, J. R. Protective Groups in Organic Synthesis; Blackwell Science: Malden, MA, 1999; (c) Hofle, G.; Steglich, W.; Vorbruggen, H. 4-Dialkylaminopyridines as highly active acylation catalysts. Angew. Chem. Int. Ed. Eng. 1978, 17, 569–583 .
  • (a) Furniss , B. S. ; Hannaford , A. J. ; Smith , P. W. G. ; Tatchell , A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed. ; Addison Wesley Longman : Harlow , England (UK) , 1997 ; pp. 1348 – 1379 ; (b) Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Ac2O–Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation. Tetrahedron Lett. 2002, 43, 4261–4265; (c) Shaffer, C. L.; Harriman, S.; Koen, Y. M; Hanzlik, R. P. Formation of Cyclopropanone during Cytochrome P450-Catalyzed N-Dealkylation of a Cyclopropylamine. J. Am. Chem. Soc. 2002, 124, 8268–8274; (d) Hwang, Y. C.; Chu, M.; Fowler, F. W. A synthesis of alpha-substituted amines. J. Org. Chem. 1985, 50, 3885–3890; (e) Hama, T.; Culkin, D. A.; Hartwig, J. F. Palladium-catalyzed intermolecular α-arylation of zinc amide enolates under mild conditions. J. Am. Chem. Soc. 2006, 128, 4976– 4985 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.