Abstract
An efficient method for the synthesis of β‐keto sulfides was developed. A thermodynamically stable enolate was generated from unsymmetrical ketones and was found to react with sulfenyl iodides generated in situ from various disulfides to give α‐sulfenylation products. Potassium tert‐butoxide was used in a solvent mixture of tBuOH/1,3‐dimethyl‐2‐imidazolidinone (DMI, 7:3) at a mild reaction temperature of 40 °C. This iodine‐catalyzed method led to products in excellent yields up to 92 % within 2 h. The method is economical and no hazardous waste products are recovered throughout the process. The protocol is important, as unmodified ketones (linear and cyclic) are easily sulfenylated, which is otherwise not trivial. The Lewis acid FeCl3 could be used as an alternative reagent to avoid the use of base and DMI. However, treatment with this Lewis acid lowered the yields and the maximum yield obtained was 85 %.
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