Synthesis of difluorinated β-ketosulfones and novel gem-difluoromethylsulfone-containing heterocycles as fluorinated building blocks

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• 作者：Hossein Loghmani-Khouzani ; Dariush Hajiheidari
• 关键词：β ; -Ketosulfones ; gem-Difluorination ; Heterocycles ; Selectfluor™ ; β ; -Ketosulfides ; Difluoromethyl sulfones
• 刊名：Journal of Fluorine Chemistry
• 出版年：2010
• 出版时间：May 2010
• 年：2010
• 卷：131
• 期：5
• 页码：561-569
• 全文大小：318 K

文摘

A series of new heterocyclic β-ketosulfides was prepared by the reaction of the corresponding heterocyclic thiols with α-bromoacetophenone and its derivatives. Oxidation of the products using m-CPBA gave the corresponding heterocyclic β-ketosulfones, which, on treatment with Selectfluor™ under anhydrous condition underwent electrophilic fluorination resulting in new heterocycles with difluoromethylene moiety adjacent to the sulfur atom and the carbonyl group. Base-induced cleavage of the five types of the resulting products, with different heterocyclic moieties as model compounds, afforded the difluoromethyl sulfones attached to the corresponding heterocycles. They can be considered as interesting fluorinated building blocks for further elaborations.