Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers.
Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes and alkynes affording only the 6-endo dig cyclization product. Additionally, a sequential indium-catalyzed IMHA and palladium-catalyzed Sonogashira coupling can be performed in one reaction vessel. Experiments with deuterium support a mechanism through electrophilic aromatic substitution.
Departamento de Química Fundamental and Centro de Investigaciones Científicas Avanzadas (CICA), Universidade da Coruña, E-15071 A Coruña, Spain. sestelo@udc.es.
Lorena
L
Alonso-Marañón
M Montserrat
MM
Martínez
Luis A
LA
Sarandeses
José Pérez
JP
Sestelo