Construction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF3-Alkenes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-08 DOI:10.1021/acs.orglett.4c04348

Sanoop P. Chandrasekharan, Usha Yadav, Kishor Mohanan

引用次数: 0

Abstract

A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving N-phenyl-α-fluoro-α-phenylsulfonylacetamide and 2-CF₃-alkenes to access N-phenyl-3,6-difluoropyridone derivatives has been achieved. The key to the success of this single-step synthesis of difluoropyridones is the strategic utilization of 2-CF₃-alkenes for consecutive allylic and vinylic substitution reactions and a desulfonylation cascade. We could also show that these difluoropyridones serve as a versatile platform for C-6-selective defluorinative functionalizations.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.