Free-Radical-Promoted β-C-H Functionalization of Simple Aliphatic Ketones, Esters, and Acids with Quinones.

Aliphatic ketones, esters, and acids are fundamental chemical raw materials in organic synthesis. The direct site-selective functionalization of such chemicals is attractive but challenging. Herein, we report a free-radical-promoted β-C-H dehydrogenative coupling reaction of simple aliphatic ketones, esters, and acids with quinones. This protocol provides a new method for the β-C-H functionalization of simple aliphatic carbonyl compounds without the assistance of exogenous directing groups and transition metals, which is different from those observed in traditional methods. In addition, the reaction realizes the challenging β-C-C bond formation of aliphatic ketones, esters, and acids, offering a promising strategy for selective alkylation of quinones.