Non-defluorinative Hydrolysis of α- and β-Fluorinated Carboxylic Acid Esters

Fluorinated carboxylic acids play a crucial role in pharmaceuticals and agrochemicals. However, the common synthetic routes involving the hydrolysis of carboxylic acid esters often face challenges such as defluorination and decarboxylation. These obstacles are overcome by utilizing an acid hydrolysis approach, leading to the selective and effective synthesis of fluorinated carboxylic acids. This method is distinguished by its high efficiency (up to 92% yield), versatility across various substrates including α- and β-fluorinated phenylacetates and α-heteroaryl esters, complete retention of fluorine substituents (non-defluorinative) in fluorinated carboxylic acid esters. Moreover, this protocol ensures complete stereoretention for chiral α-trifluoromethyl carboxylic esters and non-fluorinated carboxylic esters, further highlighting its synthetic utility in asymmetric transformations.