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An Effective Method for Acylation of Weakly Nucleophilic Anilines with Silyl Carboxylates via Mixed Anhydrides

1994; Oxford University Press; Volume: 67; Issue: 1 Linguagem: Inglês

10.1246/bcsj.67.210

1348-0634

M. Miyashita, Isamu Shiina, Teruaki Mukaiyama,

Synthetic Organic Chemistry Methods

Abstract 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 trimethylsily acetate and 4-(trifluoxomethyl)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.