Organic Letters 2011-11-18

Palladium-catalyzed decarboxylative coupling of isatoic anhydrides with arylboronic acids.

Wei Lu, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Wenxia Gao, Huayue Wu

Index: Org. Lett. 13 , 6114-6117, (2011)

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Abstract

The decarboxylative coupling of isatoic anhydrides with arylboronic acids was realized for the first time in the presence of Pd(2)(dba)(3) and DPEphos, achieving aryl o-aminobenzoates with yields ranging from moderate to good. The efficiency of this procedure was demonstrated by good compatibility with fluoro, chloro, bromo, nitro, cyano, trifluoromethyl, formacyl, acetyl, thienyl, and naphthyl groups. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.