Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles

A chemoselective C(sp(2))-C(sp(2)) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.

Automated summary

This study presents a chemoselective C(sp(2))-C(sp(2)) coupling of electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles. The fluoride-promoted transformation involves in situ generation of aryl nucleophiles with sensitive functional groups followed by a stepwise SNAr reaction. These reactions proceed rapidly at room temperature, allowing for functionalization of both coupling partners and yielding highly fluorinated biaryls in good yields.