Gold(i)-catalyzed hydroindolylation of allenyl ethersElectronic supplementary information (ESI) available: Characterization data and spectra of all new compounds. See DOI: 10.1039/c5ob00635j

The gold( i )-catalyzed reaction/rearrangement of allenyl ethers has been investigated in the presence of indoles. Either hydroindolylation or alkylation of an indole with the pendant group of allenyl ether has been observed. The reaction outcome seems to be decided mainly by the nature of the pendant group of the allenyl ether. Control experiments are indicative of an inner sphere mechanism for the hydroindolylation reaction. Nucleophilicity game : the gold( i )-catalyzed reaction/rearrangement of allenyl ethers has been investigated in the presence of indoles. The reaction outcome seems to be decided mainly by the nature of the pendant group of allenyl ether. Control experiments are indicative of an inner sphere mechanism for the hydroindolylation reaction.