Acid-catalyzed cascade ring-opening and addition reactions of arylvinylcyclopropenes with alpha,beta-unsaturated substrates, scope and limitations.
Catalyzed by Al(III) catalyst, arylvinylcyclopropenes react with alpha,beta-unsaturated substrates smoothly to produce the Diels-Alder adducts in moderate to good yields through a cascade ring-opening reaction/Diels-Alder cycloaddition. On the other hand, strong Brønsted acid TfOH can promote the cascade intramolecular Friedel-Crafts/1,4-addition reaction to produce indene derivatives in moderate to good yields under mild conditions. The acidity of the catalysts plays a key role in these reactions.
Zhu
Zhi-Bin
ZB
Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China.
Shi
Min
M