55557-15-8Relevant academic research and scientific papers
Synthesis of trimethylsilyl carboxylates by HMDS under solvent-free conditions
Jereb, Marjan,Lakner, Janja
, p. 5713 - 5723 (2016/08/23)
A broad set of structurally different carboxylic acids were transformed into their trimethylsilyl esters with HMDS in a practically completely solvent-free process, while a catalytic amount of iodine was required in some cases. The process has several advantages over the known methods: untreated reactants, air atmosphere, mild and neutral conditions, no evolution of hydrogen halide, no need of an additional base, low amount of waste, completely without chromatography, low consumption of energy, and operational simplicity.
An Effective Method for Acylation of Weakly Nucleophilic Anilines with Silyl Carboxylates via Mixed Anhydrides
Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
, p. 210 - 215 (2007/10/02)
In the presence of a catalytic amount of active titanium(IV) salt generated in situ from 1 mol of TiCl4 and 2 mol of AgOTf, weakly nucleophilic anilines react under mild conditions with nearly equimolar amounts of silyl carboxylates to afford the corresponding anilides in excellent yields using 4-(trifluoromethyl)benzoic anhydride.The mixed anhydride formed in situ from trimethylsilyl acetate and 4-(trifluoromethyl)benzoic anhydride, a key intermediate of this reaction, was detected by 1H NMR experiment.Further, it was shown that the reaction of the mixed anhydrides and 2-nitroaniline was faster than that of the corresponding homo anhydrides and 2-nitroaniline.
