Synthesis of Fluoren-9-ones Via Pd-Catalyzed Annulation of 2-Iodobiphenyls with Vinylene Carbonate.

A palladium-catalyzed reaction for intermolecular selective C-H cyclocarbonylation of 2-iodobiphenyls is described. Intriguingly, the vinylene carbonate acts as a carbon monoxide transfer agent to enable the annulation reaction. Moreover, as a versatile synthon, fluoren-9-one can be transformed into a variety of functionalized organic molecules, such as [1,1'-biphenyl]-2-carboxylic acid, 1'H,3'H-spiro[fluorene-9,2'-perimidine] and N-tosylhydrazones.