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The domino C–H/N–H allylation of aryl imidates was accomplished by a versatile cobalt(III) catalyst. In contrast to a tandem rhodium/palladium catalysis approach, an operationally simple cationic cobalt complex proved effective in the step-economical C–H/N–H functionalization of imidates to directly provide expedient access to decorated vinyl isoquinolines by kinetically relevant C–H activation.