LiO-t-Bu/CsF-Mediated Formal Hydrolysis of Trifluoromethyl Arenes

Abstract

This study investigates the formal hydrolysis of trifluoromethyl arenes without deprotonation functionality utilizing a combined Brønsted base system comprising LiO-t-Bu and CsF. The reaction conditions were optimized using 4-(trifluoromethyl)biphenyl as the model substrate, achieving a 94% yield with LiO-t-Bu/CsF. The scope of the substrate was explored, demonstrating the applicability of the system to various functionalities, such as (hetero)aryl, tert-butyl, methyl, amide, and alkenyl moieties. Mechanistic insights suggest a single electron transfer process.

Key words

trifluoromethyl arene - hydrolysis - combined Brønsted base - single-electron transfer - aromatic carboxylic acid

Publication History

Received: 23 September 2023

Accepted after revision: 28 December 2023

Accepted Manuscript online:
28 December 2023

Article published online:
01 February 2024

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