Litcius/Paper detail

O‐Trifluoromethylation of Carboxylic Acids via the Formation and Activation of Acyloxy(phenyl)trifluoromethyl‐λ <sup>3</sup> ‐Iodanes

Hongye Zhu, Chi Gao, Ting Yu, Cong Xu, Mang Wang

2024Angewandte Chemie International Edition10 citationsDOIOpen Access PDF

Abstract

Abstract Here we report the challenging O‐trifluoromethylation of carboxylic acids via the formation and activation of acyloxy(phenyl)trifluoromethyl‐λ 3 ‐iodanes. The method provides an easy access to various potentially valuable and hitherto elusive trifluoromethyl carboxylic esters. A remarkably wide range of substrates with commonly encountered functional groups are compatible with this reaction, including aromatic and aliphatic carboxylic acids, as well as Food and Drug Administration (FDA) approved drugs and pharmaceutically relevant molecules. The reaction mechanism and the origins of the enhanced reactivity by zinc chloride (ZnCl 2 ) were discussed from experimental evidence and density functional theory (DFT) calculation.

Topics & Concepts

TrifluoromethylationTrifluoromethylChemistryMedicinal chemistryOrganic chemistryAlkylFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsInorganic Fluorides and Related Compounds