Acid-Catalyzed Solvent-Switchable Chemoselective -Alkylation and -Alkylation of Unprotected Arylamines Utilizing -Quinone Methides.

Nitrogen-containing compounds, such as anilines, represent some of the most prevalent and valuable chemical entities within the field of chemistry. However, their high reactivity, which frequently lacks selectivity, has constrained their application in various chemical transformations, including the alkylation of alcohols. In the present study, we successfully accomplished site-selective and N-H alkylation of anilines by utilizing -quinone methides under mild conditions.

Chemoselective deoxygenative α-arylation of carboxylic acids, amides, and esters: synthesis of anesthetic and anti-inflammatory compounds.

A metal-free strategy has been developed for the α-arylation of carboxylic acids, secondary amides, and esters employing arenes as key reagents. This process entails the Lewis-acid catalyzed reductive Friedel-Crafts alkylation of arenes utilizing α-ketoacids, facilitated by silane in HFIP solvent. The transformation exhibits exceptional functional group tolerance, enabling late-stage functionalization of natural products.