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Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts

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Abstract Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides R F I or sodium perfluoroalkylsulfinate salts NaSO 2 R F as perfluoroalkyl… Click to show full abstract

Abstract Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides R F I or sodium perfluoroalkylsulfinate salts NaSO 2 R F as perfluoroalkyl R F radical precursors is presented. The electron-catalyzed methodologies make use of two comparative and parallel protocols as an entry to the production of R F radicals: (i) from NaSO 2 R f sources and the thermal tert -butylhydroperoxide (TBHP) radical initiation in MeCN: CH 2 Cl 2 as organic solvent mixture, and (ii) from commercial R F I and the photoorganocatalyst anthraquinone-2-sulfonic acid as the room-light initiation process in DMF: CH 2 Cl 2 as mixture of solvents.

Keywords: late stage; electron catalyzed; perfluoroalkyl; sodium; coumarin derivatives

Journal Title: Journal of Fluorine Chemistry
Year Published: 2017

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