Nucleophilic C-H functionalization of arenes: A new logic of organic synthesis Expanding the scope of nucleophilic substitution of hydrogen in aromatics

Abstract

Direct metal-free C-H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the SN H reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C-H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The SN H reactions, as a part of the general C-H functionalization concept, change the logic of organic synthesis. They open new opportunities, avoiding incorporation of good leaving groups or other auxiliaries in an aromatic ring, as a prefunctionalization step, thus providing a better correspondence to the principles of green chemistry. © 2017 IUPAC & De Gruyter.