Open AccessCation Radical-Accelerated Nucleophilic Aromatic Substitution for Amination of Alkoxyarenes
Author(s) -
Nicholas J. Venditto,
David A. Nicewicz
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01621
Subject(s) - nucleophilic aromatic substitution , chemistry , amination , radical nucleophilic aromatic substitution , nucleophilic substitution , nucleophile , electrophilic aromatic substitution , ether , combinatorial chemistry , substitution reaction , aryl , oxidizing agent , medicinal chemistry , organic chemistry , photochemistry , catalysis , alkyl
Nucleophilic aromatic substitution (S N Ar) is a common method for arene functionalization; however, reactions of this type are typically limited to electron-deficient aromatic halides. Herein, we describe a mild, metal-free, cation-radical accelerated nucleophilic aromatic substitution (CRA-S N Ar) using a potent, highly oxidizing acridinium photoredox catalyst. Selective substitution of arene C-O bonds on a wide array of aryl ether substrates was shown with a variety of primary amine nucleophiles. Mechanistic evidence is also presented that supports the proposed CRA-S N Ar pathway.