An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

Abstract

Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.

Iron (III) Phosphate as a Green and Reusable Catalyst Promoted Chemo Selective Acetylation of Alcohols and Phenols with Acetic Anhydride Under Solvent Free Conditions at Room Temperature

“…As can be seen, the yields of the acetylation hydroxyl group compounds with acetic anhydride were excellent. Accordingly, various primary and secondary benzyl alcohols having electron donating and electron withdrawing substituent undergo acetylation in high yield in most cases (entries [10][11][12][13][14][15]. This indicates that electronic effects of substituent groups don't have influence on the acetylation reaction.…”

Selective Acetylation of 2-Naphthol to 2-Naphthyl Acetate with Ni Homogeneous Catalysts: An Environmentally Friendly Protocol

“…Number of lewis acids such as TMSCl [15][16] [22]. Since a few past years, it has been reported that several metal triflates such as In(OTf) 3 [30], Bi(OTf) 3 [31], ZrO(OTf) 2 [32], Gd(OTf) 3 [33], as well as Me 3 SiOTf [34][35] are excellent catalysts for efficient acetylation of various types of structurally diverse alcohols with aceticanhydride. Cu(OTf) 2 (TfCF 3 SO 2 ) [23], Er(OTf) 3 [24], Al(OTf) 3 [25], Ti-Cl 3 (OTf) [9], Ce(OTf) 3 [21], SnIV(tpp)(OTf) 2 (tpp = tetra phenylporphyrin) [26].…”

Acetylation of alcohols, phenols and salicylic acid by heteropoly acids in acetic anhydride: a green and eco-friendly protocol for synthesis of acetyl salicylic acid (Aspirin)

“…The most commonly used reagent combination for this reaction uses acid anhydride in the presence of acid or base catalysts 2 . Various metal salts such as CoCl 2 3 , TiCl 4 -AgClO 4 4 , TaCl 5 and TaCl 5 -SiO 2 5 , Ce(III) triflate 6 , Sn(IV) porphyrine 7 and some metal triflates such as Sc(OTf) 3 8 MeSiOTf 9 , In(OTf) 3 10 , Cu(OTf) 2 11 and Bi(OTf) 3 12 bis(cyclopentadienyl) zirconium dichloride 13 , I 2 14 , 1,3-dibromo-5,5-dimethylhydentoin or trichloroisocyanuric acid 15 have been investigated to meet the demand for more efficient and selective methods. In spite of these waves of interest due to the importance of acetylation, introduction of inexpensive and green catalyst for this purpose is still in much demand.…”