Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers

作者:Alonso Maranon Lorena; Montserrat Martinez M; Sarandeses Luis A; Perez Sestelo Jose
来源:Organic and Biomolecular Chemistry, 2015, 13(2): 379-387.
DOI:10.1039/c4ob02033b

摘要

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.

  • 出版日期2015