Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C−H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.
All Science Journal Classification (ASJC) codes
- Organic Chemistry