Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE

Alain Gamal Giuglio-Tonolo (1) , Thierry Terme (1) , Patrice Vanelle (1)

1 ICR - Institut de Chimie Radicalaire

We report here a novel and easy-to-handle reductive dehalogenation of 9-bromofluorene in the presence of arylaldehydes and dicarbonyl derivatives to give the corresponding fluorenyl alcohol derivatives and Darzens epoxides as by-products in tetrakis(dimethylamino)ethylene (TDAE) reaction conditions. The reaction is believed to proceed via two successive single electron transfers to generate the fluorenyl anion which was able to react with different electrophiles. A mechanistic study was conducted to understand the formation of the epoxide derivatives.

Mots clés: tetrakis(dimethylamino)ethylene; reductive dehalogenation; single electron transfer

Domaines: Chimie

Alain Gamal Giuglio-Tonolo, Thierry Terme, Patrice Vanelle. Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE. Molecules, 2016, 21 (10), ⟨10.3390/molecules21101408⟩. ⟨hal-01785575⟩