Complementary to standard Birch reduction, rAP reduction is most suitable for electron-deficient (hetero)arenes. The success of the reaction is predictable based on the reduction potential of an arene and a functional group that can be easily measured using CV (empirical guidance for FG tolerance is summarized in Table ). Thus, synthetically useful yields are obtained when a target arene has a more positive reduction potential than those of other functional groups (Ered,arene > E red,FG). As such, electron-deficient heteroarenes exhibit the broadest functional group tolerance with ester (5-10, 12, 14-16), nitrile (7), allyl group (11), epoxide (8) and even alkyl chloride (13). Electron-deficient arenes are slightly less reducible than electron-deficient heterocycles, and the functional group compatibility of this class is more limited. Nevertheless, synthetically useful handles such as allyl (21), alkyne (22), ester (23, 24, 27), boronate ester (25), alkyl chloride (26) and nitrile (27, 28) were well-