Rhodium-catalyzed coupling of arenes and fluorinated α-diazo diketones: synthesis of chromones

Rhodium(iii)-catalyzed C-C coupling of heteroarenes and fluorinated alpha -diazo diketones has been realized for the facile synthesis of 3-arylchromones. The reaction proceeds via chelation-assisted C-H activation, carbene insertion, and uncatalyzed intramolecular nucleophilic aromatic substitution, with C-F cleavage being accommodated in the nucleophilic aromatic substitution step. Three classes of heteroarenes have been defined with decent functional group tolerance.