ABSTRACT
Functionalization of aromatic compounds using Friedel-Crafts chemistry is accompanied by a large amount of waste. The Heck reaction is an industrially viable alternative for carbon carbon bond formation to arenes. However, all existing methods make use of halide containing arylating agents such as aryl iodides and bromides, which also leads to salt waste. This dilerruna was solved by the invention of aromatic anhydrides as the aryl donor. This new decarbonylative Heck reaction is catalyzed by PdCh, which is promoted, ironically, by a small amount of halide salt such as chloride or bromide. Benzoic acid, which is recycled to the anhydride and CO, which is burned to C02 are the only side products. The reaction needs neither bases nor phosphine ligands. Olefins with electron-withdrawing groups are excellent substrates, but electrondonating substituents gave rise to poor yields of the a-arylated olefms. Unsubstituted olefms are rapidly isomerized leading to isomeric mixtures of arylation products. The mechanism is still under investigation.
