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Stereocontrolled synthesis of benzo[k]fluoranthenes--an unexpected isomerization mediated by rhodacyclopentadiene.

Herein, a Rh(III) -catalyzed stereocontrolled synthesis of benzo[k]fluoranthenes is reported. It was found that the unexpected E/Z isomerization was highly sensitive to the electronic effects of the substituents on the aryl groups. Theoretical calculations revealed that this controllable stereochemistry originates from the mediation of rhodacyclopentadiene intermediates during the isomerization. The fact that similar stereochemistry was observed when using an Ir(III) catalyst further suggests a certain generality of this discovery toward some other transition metals.