Highly Site-Selective Metal-Free C–H Acyloxylation of Stable Enamines

• DOI: 10.1021/acs.orglett.8b00222
• Publication Date: 2018-02-08T15:19:21Z
• Authors: Fei Wang; Wangbing Sun; Yixin Wang; Yaojia Jiang; Teck-Peng Loh
• Keywords: Amide; Reaction conditions

A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good excellent yields is described. Depending on the judicious choice solvent system, either α- or β-site-selective product could be obtained high selectivity. For α-site-selective product, rearranged amide compound as major product. This reaction proceeds mild (room temperature, metal-free, and open-flask) features a broad substrate scope.