Three-Component Sulfonylation and Heteroannulation Enabled by 3-Fold Defluorofunctionalization of Trifluoromethyl Enones

Shu Ji Gao, Xue Ying Huang, Xiao Ying Li, Danhua Ge, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

Research output: Contribution to journalArticlepeer-review

Abstract

Trifluoromethyl enone emerges as a versatile and multifaceted building block in organic synthesis. A defluorinative heterocyclization reaction of readily available β,β-ditrifluoromethylated enones and biocompatible sodium sulfinates has been developed for the modular synthesis of densely functionalized furans with regio-defined C2,4-bissulfonyl and C3-trifluoromethyl substitutions. This three-component method proceeds through a sequential sulfonylation and intramolecular O-cyclization, enabling the assembly of one furan ring, the formation of C-SO2/C-O bonds, and the cleavage of three C(sp3)-F bonds in a one-pot manner under transition metal-free conditions. Moreover, the obtained furan product can further react with a benzyne precursor to generate 1,4-epoxynaphthalene through a Diels-Alder cycloaddition. The reaction is also distinguished by its broad substrate scope, excellent functional group tolerance, and scalability.

Original languageEnglish
Pages (from-to)3373-3383
Number of pages11
JournalJournal of Organic Chemistry
Volume90
Issue number9
DOIs
StatePublished - 7 Mar 2025

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