Abstract
AbstractUse of the hypervalent aryl‐λ3‐iodane reagent iodobenzene dichloride (PhICl2) in the α‐carbonyl dichlorination of 2‐oxindoles is reported. Treating a series of diversely substituted 3‐diazo‐2‐oxindoles with PhICl2 in the presence of pyridine, a Lewis base iodane‐activator, results in 3,3‐dichloro‐2‐oxindole products. Activation of PhICl2 is key to the chlorination proceeding rapidly, chemoselectively and in good to excellent yields. This investigation represents a novel approach to the synthesis of 3,3‐disubstituted‐2‐oxindoles, and illustrates the compatibility of the ligand‐transfer reaction with the 2‐oxindole scaffold.magnified image
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