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

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Rhodium(iii)-catalyzed C-C coupling of heteroarenes and fluorinated α-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… Click to show full abstract

Rhodium(iii)-catalyzed C-C coupling of heteroarenes and fluorinated α-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.

Keywords: rhodium catalyzed; coupling arenes; catalyzed coupling; fluorinated diazo; diazo diketones; synthesis

Journal Title: Chemical communications
Year Published: 2020

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