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Visible light-driven photocatalysis enables tunable stereoselective trifluoromethylation of styrenes, selectively yielding E-alkenes using Togni's reagent with Ru(bpy)3Cl2·6H2O, and Z-alkenes using Umemoto's reagent with Ir(ppy)3. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

October 8, 2014The Journal of Organic Chemistry138 citations

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Chemo-, Regio-, and Stereoselective Trifluoromethylation of Styrenes via Visible Light-Driven Single-Electron Transfer (SET) and Triplet–Triplet Energy Transfer (TTET) Processes

QLQingyu LinSun Yat-sen University XXXiu‐Hua XuShanghai Institute of Organic Chemistry FQFeng‐Ling QingChinese Academy of Sciences

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Abstract

A process for tunable and chemo-, regio-, and stereoselective photocatalytic trifluoromethylation of styrenes was developed. Thermodynamically stable E-trifluoromethylated alkenes were prepared using Togni's reagent in the presence of Ru(bpy)3Cl2·6H2O under visible light irradiation, whereas less thermodynamically stable Z-trifluoromethylated alkenes were obtained by employing Umemoto's reagent and photocatalyst Ir(ppy)3.

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Chemo-, Regio-, and Stereoselective Trifluoromethylation of Styrenes via Visible Light-Driven Single-Electron Transfer (SET) and Triplet–Triplet Energy Transfer (TTET) Processes

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