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 language | English |
---|---|
Pages (from-to) | 3373-3383 |
Number of pages | 11 |
Journal | Journal of Organic Chemistry |
Volume | 90 |
Issue number | 9 |
DOIs | |
State | Published - 7 Mar 2025 |