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Am ild and metal-free method to functionalize aliphatic CÀHb onds adjacent to an itrogen atom through radical translocation, oxidation to an iminium intermediate, and nucleophilic trapping with alcohols is described. The transformation proceeds efficiently with edible ascorbic acid (vitamin C) as the radical initiator andr eadily available tert-butyl nitrite as the nitrosating reagent. Notably,a ny transition-metal or additive is not required. The current methodp rovides simple, efficient, and practical access to valuable a-alkoxybenzamides in moderatet o good yields.Scheme1.Strategies for the preparation of a-substituted benzamides through radical translocation. AIBN = azobisisobutyronitrile;E WG = electronwithdrawing group.

A Mild, Efficient, and Practical Approach to -Alkoxybenzamides. -Cyclic and acyclic 2-aminobenzoic acid amides are -alkoxylated by a variety of alcohols using tBuONO as nitrosating agent and ascorbic acid as radical initiator. During the reaction, the ortho-amino group is transformed into a diazonium function that is radically eliminated by ascorbic acid. -(HUANG, F.-Q.; ZHOU, G.-X.; DONG, X.; QI*, L.-W.; ZHANG, B.; Asian J. Org. Chem. 5 (2016) 2, 192-195, http://dx.