How do you reduce aromatic rings?

Birch reduction uses alkali metals and a proton source (usually ethanol or tert-butanol) to convert SOME aromatic compounds into 1,4-cyclohexadienes.

With catalytic hydrogenation, of course, a brute force method could be used. However, such a reduction would be extremely indiscriminate and require forcing conditions.

Aromatic rings can be reduced using various chemical reagents, such as hydrogen gas in the presence of a metal catalyst like platinum or palladium, or using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) in appropriate solvents. These reagents donate electrons to the aromatic ring, leading to the formation of cyclohexadienes or cyclohexanes, depending on the reaction conditions. Additionally, Birch reduction, which involves the use of liquid ammonia (NH3) and an alkali metal such as sodium or lithium in the presence of an alcohol, is commonly employed for selective reduction of aromatic rings.