Small organic molecules with tailored structures: initiators in the transition-metal-free C-H arylation of unactivated arenes.

ABSTRACT: Simple, small organic molecules containing nitrogen and oxygen atoms in their structures have been disclosed to catalyze transition-metal-free C-H arylation of unactivated arenes with aryl iodides in the presence of ^t BuOK. In this article, an optimized catalytically active molecule, (2-(methylamino)phenyl)methanol, was designed. A broad range of aryl iodides could be converted into the corresponding arylated products at 100 °C over 24 h with good to excellent yields. Mechanistic experiments verified that radicals participated in this catalytic transformation and that the cleavage of the aromatic C-H bond was not the rate determining step. A K⁺ capture experiment by 18-crown-6 emphasized the significance of the cation species of the strong base. Fourier transfo

SUBMITTER: Liu Z 

PROVIDER: S-EPMC9051888 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature