Alonso-Marañón, LorenaMartínez, M. MontserratSarandeses, Luis A.Gómez Bengoa, EnriquePérez Sestelo, José2024-02-022018-06-12Alonso-Marañón, L., Martínez, M. M., Sarandeses, L. A., Gómez-Bengoa, E., and Pérez Sestelo, J. (2018). Indium(III)-Catalyzed Synthesis of Benzo[b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights. The Journal of Organic Chemistry, 83(15), 7970-7980. https://doi.org/10.1021/acs.joc.8b008291520-6904http://hdl.handle.net/2183/35379[Abstract] Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.eng© 2018 American Chemical SocietyAnionsAromatic compoundsHydrocarbonsIndiumInorganic compoundsjournal articleembargoed access10.1021/acs.joc.8b00829