86569-53-1Relevant articles and documents
An Effective Method for Acylation of Weakly Nucleophilic Anilines with Silyl Carboxylates via Mixed Anhydrides
Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
, p. 210 - 215 (1994)
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.
A Convenient Synthesis of Carboxanilides from Silyl Carboxylates and Weakly Nucleophilic Anilines Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Titanium(IV) Salt
Miyashita, Mitsutomo,Shiina, Isamu,Mukaiyama, Teruaki
, p. 1053 - 1054 (2007/10/02)
Various carboxanilides are prepared in excellent yields from nearly equimolar amounts of silyl carboxylates and the corresponding weakly nucleophilic anilines under mild conditions by using p-trifluoromethylbenzoic anhydride and a catalytic amount of active titanium(IV) salt.
