Copper and Photocatalytic Radical Relay Enabling Fluoroalkylphosphorothiolation of Alkenes: Modular Synthesis of Fluorine-Containing S‑Alkyl Phosphorothioates and Phosphorodithioates
journal contributionposted on 15.11.2021, 12:36 by Pengbo Zhang, Wenwu Li, Weilong Qu, Zhigang Shu, Yingjun Tao, Jinming Lin, Xia Gao
A photoredox and copper-catalyzed fluoroalkylphosphorothiolation of activated and unactivated alkenes via a radical relay mechanism is reported. By employing fluoroalkyl halides as radical precursors and P(O)SH or P(S)SH compounds as coupling partners, a wide range of β-monofluoroalkyl-, -difluoroalkyl-, -trifluoromethyl-, or -perfluoroalkyl-substituted S-alkyl phosphorothioates and phosphorodithioates can be easily constructed under mild conditions with good functional group tolerance. Furthermore, this modular reaction system can be successfully applied to late-stage functionalization of bioactive molecules.
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employing fluoroalkyl halides>‑ alkyl phosphorothioates>- alkyl phosphorothioatesradical relay mechanismmodular reaction systemunactivated alkenes via) sh compounds) shradical precursorsmodular synthesiswide rangetrifluoromethyl -,successfully appliedstage functionalizationp (monofluoroalkyl -,mild conditionseasily constructeddifluoroalkyl -,coupling partnerscatalyzed fluoroalkylphosphorothiolationbioactive molecules