Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 7
513
Views
21
CrossRef citations to date
0
Altmetric
Original Articles

Bismuth(III) Triflate: A Safe and Easily Handled Precursor for Triflic Acid: Application to the Esterification Reaction

, , &
Pages 1082-1087 | Received 10 Feb 2009, Published online: 04 Mar 2010

REFERENCES

  • Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis, , 3rd ed. ; John Wiley & Sons : New york , 1999 , and references cited therein .
  • (a) Leonard , N. M. ; Wieland , L. C. ; Mohan , R. S. Applications of bismuth(III) compounds in organic synthesis . Tetrahedron 2002 , 58 , 8373 – 8397 ; (b) Gaspard-Iloughmane , H. ; Le Roux , C. Bismuth(III) triflate in organic synthesis . Eur. J. Org. Chem. 2004 , 2517 – 2532 .
  • Lherbet , C. ; Soupaya , D. ; Baudoin-Dehoux , C. ; André , C. ; Blonski , C. ; Hoffmann , P. Bismuth triflate- catalyzed oxa- and thia-Pictet–Spengler reactions: Access to iso- and isothio-chroman compounds . Tetrahedron Lett. 2008 , 49 ( 38 ), 5449 – 5451 .
  • Buzin , P. ; Lahcini , M. ; Schwarz , G. ; Kricheldorf , H. R. Aliphatic polyesters by bismuth triflate–catalyzed polycondensations of dicarboxylic acids and aliphatic diols . Macromolecules 2008 , 41 , 8491 – 8495 .
  • (a) Orita , A. ; Tanahashi , C. ; Kakuda , A. ; Otera , J. High efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst . Angew. Chem. Int. Ed. 2000 , 39 , 2877 – 2879 ; (b) Carrigan , M. D. ; Freiberg , D. A. ; Smith , R. C. ; Zerth , H. M. ; Rohan , R. S. A simple and practical method for large-scale acetylation of alcohols and diols using bismuth triflate . Synthesis 2001 , 2091 – 2094 ; (c) Nagano , Y. ; Orita , A. ; Otera , J. Combined Lewis acid catalysts in shotgun process: A convenient synthesis of the female sex pheromone of the red-bollworm mouth . Tetrahedron 2002 , 58 , 8211 – 8217 .
  • Dumeunier , R. ; Markó , I. E. On the role of triflic acid in the metal triflate-catalysed acylation of alcohols . Tetrahedron Lett. 2004 , 45 , 825 – 829 .
  • Bizier , N. P. ; Atkins , S. R. ; Helland , L. C. ; Colvin , S. F. ; Twitchell , J. R. ; Cloninger , M. J. Indium triflate–catalyzed peracetylation of carbohydrates . Carbohydr. Res. 2008 , 343 , 1814 – 1818 .
  • Ollevier , T. ; Nadeau , E. An efficient and mild bismuth triflate–catalysed three-component Mannich-type reaction . Org. Biomol. Chem. 2007 , 5 , 3126 – 3134 .
  • Navath , R. S. ; Pabbisetty , K. B. ; Longqin , H. Chemoselective deprotection of N-Boc group in amino acids and peptides by bismuth(III) trichloride . Tetrahedron Lett. 2006 , 47 , 389 – 393 .
  • Morgan , D. O. ; Ollis , W. D. ; Stanforth , S. P. Preparation and cycloaddition reactions of novel heterocyclic mesomeric betaines . Tetrahedron 2000 , 56 , 5523 – 5534 .
  • Mineno , T. ; Kansui , H. High-yielding methyl esterification catalyzed by indium(III) chloride . Chem. Pharm. Bull. 2006 , 54 , 918 – 919 .
  • Dixon , R. W. ; Radmer , R. J. ; Kuhn , B. ; Kollman , P. A. Theoretical and experimental studies of biotin analogues that bind almost as tightly to streptavidin as biotin . J. Org. Chem. 2002 , 67 , 1827 – 1837 .

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.