Mechanistic studies on fluorocyclohexene conversion to fluorobenzene under Pd-catalyzed dehydrogenation

The chemical reactivity and reaction mechanism of fluorobenzene formation by dehydrogenation of fluorocyclohexenes was investigated. 1-Fluorocyclohexene reacted with oxidants such as nitrobenzene and oxygen to give fluorobenzene in good yields under moderate conditions in the presence of a Pd catalyst. A detailed comparison of oxidative dehydrogenation with non-oxidative dehydrogenation proved that the oxidants effectively suppressed isomerization and disproportionation, and offered a selective synthesis of fluorobenzene.

The chemical reactivity and reaction mechanism of fluorobenzene formation by dehydrogenation of fluorocyclohexenes are described. The oxidants effectively suppressed isomerization and disproportionation, and offered a selective synthesis of fluorobenzene.Figure optionsDownload high-quality image (73 K)Download as PowerPoint slideResearch highlights
► Pd as dehydrogenation catalyst.
► Catalysts for dehydrogenation of fluorocyclohexenes.
► Fluorobenzene formation by dehydrogenation of fluorocyclohexenes.
► Oxidants effectively suppressed isomerization and disproportionation.