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

M Miyashita, I Shiina, T Mukaiyama

Index: Miyashita, Mitsutomo; Shiina, Isamu; Mukaiyama, Teruaki Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 1 p. 210 - 215

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Citation Number: 22

Abstract

In the presence of a catalytic amount of active titanium (IV) salt generated in situ from 1 mol of TiCl 4 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 ...