Oxidative C–H Acyloxylation of Acetone with Carboxylic Acids under Iodine Catalysis

Abstract

Iodine-catalyzed oxidative C(sp3)–H acyloxylation of acetone with carboxylic acids has been developed. The method employs iodide­ as catalyst and sodium chlorite as oxidant. Substituted benzoic acids, naphthoic acids and heteroaromatic carboxylic acids can be used, and 2-oxopropyl carboxylates are obtained with good to excellent yields.

α-Acyloxylation of Ketones/Cyclic Ethers Mediated by Hypervalent Iodine(III) Reagents as Oxidants and Nucleophilic Sources

“…Thus, many methods have been developed to prepare them, with most methods relying on preactivation strategies or metal-catalyzed coupling reactions . In recent years, to circumvent the use of metals and toxic reagents, metal-free α-acyloxylations of ketones/cyclic ethers with carboxylic acids using Bu 4 NI/TBHP, KI/K 2 S 2 O 8 , KI/1,2-dibromoethane, NCS/Na 2 CO 3 , NCS/NaOAc, I 2 /NaClO 2 , and electrochemical benzylic C–H acyloxylation have been disclosed. Meanwhile, asymmetric methods for synthesizing α-acyloxycarbonyl compounds from ketones or aldehydes have also been developed.…”