Photocatalytic Trifluoromethyl Carbyne Equivalent Generation: A Modular Platform for Cascade Cycloannulation
Zhi-Yu Lang1, Li-Ping Tu1, De-Xia Lin1
1Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi 563006, P. R. China.
Abstract:
A visible-light-induced radical cascade cyclization of N-aryl acrylamides with trifluoromethyl carbyne equivalents is described, affording structurally diverse trifluoromethylated oxindoles bearing a diazo moiety. This first carbyne-equivalent-mediated radical cascade reaction proceeds through a diazotrifluoroethyl radical intermediate, exhibiting broad substrate scope, excellent functional group tolerance, and high regioselectivity. Mechanistic investigations support a radical mechanism involving a reductive quenching cycle. Gram-scale synthesis and product derivatizations demonstrate the synthetic utility, establishing a new platform for both fluorinated heterocycle synthesis and carbyne chemistry.
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