Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

ABSTRACT: The amination of aryl halides has become one of the most commonly practiced C-N bond-forming reactions in pharmaceutical and laboratory syntheses. The widespread use of strong or poorly soluble inorganic bases for amine activation nevertheless complicates the compatibility of this important reaction class with sensitive substrates as well as applications in flow and automated synthesis, to name a few. We report a palladium-catalyzed C-N coupling using Et₃N as a weak, soluble base, which allows a broad substrate scope that includes bromo- and chloro(hetero)arenes, primary anilines, secondary amines, and amide type nucleophiles together with tolerance for a range of base-sensitive functional groups. Mechanistic data have established a unique pathway for these reactions in which wa

SUBMITTER: Lau SH 

PROVIDER: S-EPMC7690001 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature