Metal-Free, Hindered, Regioselective Access to Multifunctional Groups Diarylamines via SN Ar Substitution of P-Nitroso Aromatic Methyl Ether by Arylamines

Abstract

Multifunctional groups diarylamines, an innovative product, efficiently produced from arylamines and p-nitrosoanisole derivatives by intermolecular S_N Ar under weak acid conditions. This S_N Ar proceeds under mild reaction conditions, and more significantly, the substrates involved do not necessarily require strong electron-withdrawing groups. Moreover, this S_N Ar is characterized by resistance to space crowding, tolerance to halogen and nitroso functional groups, and high regioselectivity. Mechanistic observations suggest that the S_N Ar is the result of the transfer of the positive charge center of the protonated nitroso group to the p-methoxy group.

Keywords: amination; hindered; intermolecular nucleophilic aromatic substitution; nitroso arenes; regioselective.