Ethyl diazoacetate, reaction with indole

Methoxy-, methyl- and bromo-substituted indoles also participated readily in a tandem palladium/copper catalyzed C—H functionalization/ C—H insertion reaction with ethyl diazoacetate (147) and iodobenzene (146) (2015JAC4435). More significantly, the authors were able to illustrate that a copper catalyzed N—H insertion could also be performed in tandem with the C—H functionalization. In this case, 4-aminoindole (149) smoothly underwent coupling to give 150 in 79% yield. 

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