eFluorination for the Rapid Synthesis of Fluorothioformates from Oxalic Acid Monothioesters

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

An efficient and practical electrochemical method for synthesizing fluorothioformate derivatives, an underexplored functional group, is reported. The strategy based on the anodic decarboxylation of oxalic acid monothioesters, which rapidly generates highly reactive alkyl (oxomethylidene)sulfonium intermediates. These intermediates are effectively trapped by inexpensive commercially available triethylamine trihydrofluoride (Et3N·3HF), acts as both a nucleophilic fluoride source supporting electrolyte, leading to formation desired fluorothioformates. This methodology enables rapid scalable synthesis enabling their broader exploration in organic chemistry. In particular, these compounds can be readily selectively converted S-thiocarbamates urea derivatives one-pot process through reactions with amines, demonstrating synthetic utility. scalability this fluorination was validated, showing no loss yield. Cyclic voltammetry studies were carried out shed some light mechanism novel transformations.

Язык: Английский

Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p-Methoxybenzyl Esters

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7956 - 7960

Опубликована: Сен. 11, 2024

A new strategy for the metal-free photoinduced activation of

Язык: Английский

Chemoselective Cleavage and Transamidation of Tertiary p-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

A metal-free and mild cleavage of tertiary

Язык: Английский