Chemistry Letters, Vol.46, No.7, 926-929, 2017
Rhodium-catalyzed Carbonylative Annulation of 2-Bromobenzylic Alcohols with Internal Alkynes Using Furfural via beta-Aryl Elimination
In spite of the significant progress made in transformations of unstrained benzylic (tert-) alcohols through beta-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over beta-aryl elimination. In this letter, we report on the rhodium(I)-catalyzed carbonylative annulation of alpha,alpha-dimethyl-(2-bromoaryl) methanols with internal alkynes using furfural leading to the formation of indenones. The key to the success of the reaction is the timely generation of the carbonyl source via the decarbonylation of furfural.