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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Access to Alkylative/Hydrodefluorination of Trifluoromethyl Ketones Using Photoexcited Dihydropyridines
Surajit Das1, Debasis Maity1, Biprajit Paul1
1Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar, Punjab-140001, India.
Abstract:
A convenient strategy for selective and challenging single C-F bond functionalization of trifluoromethyl ketones has been introduced under visible light irradiation. Photoexcited 1,4-DHP serves a dual purpose as a reductant and a source of alkyl radicals (or H atoms) in the alkylative defluorination and hydrodefluorination processes. The solvent hexafluoroisopropyl alcohol (HFIP) plays a crucial role in the selective single C-F bond cleavage. Overall, a transition-metal- and photocatalyst-free, mild protocol for accessing a broad range of functionalized fluorinated products of high pharmaceutical interest is presented here. Operational simplicity and mechanistic evidence for photoinduced alkyl (or HAT) radical generation highlight the effectiveness of this strategy as a reliable toolbox for selective defluorinative C-C cross-coupling and a hydrodefluorination protocol.
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