Supercritical carbon dioxide as reaction medium for selective hydrogenation of fluorinated arenes

The selective hydrogenation of fluorinated arenes with polar functionalities is achieved, opening a versatile pathway for the production of valuable substituted fluorocyclohexane derivatives from readily available substrates. The use of supercritical carbon dioxide (scCO(2)) as a hydrophobic and green solvent in combination with Rh nanoparticles immobilized on molecularly modified silica as catalysts favours hydrogenation over hydrodefluorination. The approach compares favourably in terms of green chemistry metrics relative to traditional synthetic routes as exemplified for the useful building block 4-fluorocyclohexan-1-ol.

Automated summary

The selective hydrogenation of fluorinated arenes with polar functionalities provides a versatile pathway for the synthesis of valuable substituted fluorocyclohexane derivatives. The use of supercritical carbon dioxide (scCO(2)) as a hydrophobic and green solvent, in combination with Rh nanoparticles immobilized on molecularly modified silica as catalysts, favors hydrogenation over hydrodefluorination. This approach compares favorably to traditional synthetic routes in terms of green chemistry metrics, as demonstrated for the synthesis of 4-fluorocyclohexan-1-ol, a useful building block.