Benzoylating methoxybenzene derivation by bismuth triflate under microwave irradiation

Hoang Phuong Tran, Truong Hai Nguyen, Ngoc Thach Le

Main Article Content

Abstract

An efficient bismuth trifluoromethanesulfonate-catalyzed benzoylation of aromatic compounds and benzoic anhydride under microwave-irradiated solvent-free have been developed. Under solventless conditions, this process grants the preparation of aryl ketones in good yields and short reaction time. Especially, after reaction, Bi(OTf)3-catalyzed is easily recovered and reused five times without yield loss of the catalytic activity.

Article Details

References

[1]. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. (2003), “Solvent-free Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of trifl uoroacetic anhydride and aluminum dodecatungstophosphate”, Tetrahedron Letters, (44), p. 5343-5345.
[2]. Kawamura, M.; Cui, D.-M.; Hayashi, T.; Shimada, S. (2003), “Lewis acid-catalyzed Friedel-Crafts acylation reaction using carboxylic acids as acylating agents”, Tetrahedron Letters, (44), p. 7715-7717.
[3]. Kobayashi, S. (1999), “Scandium Trifl ate in Organic Synthesis”, European Journal of Organic Chemistry, (1999), p. 15-27.
[4]. Matsushita, Y.-i.; Sugamoto, K.; Matsui, T. (2004), “The Friedel-Crafts acylation of aromatic compounds with carboxylic acids by the combined use of perfl uoroalkanoic anhydride and bismuth or scandium trifl ate”, Tetrahedron Letters, (45), p. 4723-4727.
[5]. Mona Hosseini Sarvari, H. S. (2004), “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, (13), p. 2165-2168.
[6]. Tran, P. H.; Hansen, P. E.; Nguyen, H. T.; Le, T. N. (2015), “Erbium trifl uoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation”, Tetrahedron Letters, (56), p. 612-618.
[7]. Wang, Z. (2010), “Friedel-Crafts Acylation”, Comprehensive Organic Name Reactions and Reagents, Wiley, p. 1126-1130.