Regioselective Difunctionalization of gem-Difluorocyclopropanes via Palladium-Catalyzed Defluorinative Coupling
Chao Yang1, Liliang Huang1, Youcan Zhang1
1College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.
Abstract:
gem-Difluorocyclopropanes (gem-DFCPs) serve as versatile building blocks in synthetic chemistry, generally enabling the preparation of functional molecules through ring-opening substitution. Here, we disclose an efficient palladium-catalyzed difunctionalization of gem-DFCPs using alcohols or phenols as nucleophiles to construct alkoxy- or aryloxy-functionalized allyl ethers. This reaction is operationally simple, displays broad functional group tolerance, and exhibits excellent chemo- and regioselectivity. Investigations into the mechanism suggest that the secondary C-F substitution proceeds via a monofluorinated four-membered palladacycle intermediate.
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