N-Trifluoroethoxyphthalimide

CAS 76029-67-9, Cat. No EN300-18981232
Reagent for trifluoromethylation

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N-Trifluoroethoxyphthalimide is a redox-active reagent that generates α-hydroxytrifluoroethyl radicals. In nickel-catalyzed reductive cross-electrophile coupling with iodoarenes¹, it provides α-aryl-α-trifluoromethyl alcohols in good yields (up to 88%) with broad scope, tolerating both electron-rich and electron-poor aryl iodides, halogens, esters, and ketones, enabling late-stage functionalization of bioactive scaffolds. Another methodology utilizes dual nickel/photoredox catalysis² leading to enantioenriched α-trifluoromethyl acyloins (up to 95% yield, 92% ee), which can be reduced to anti-1,2-diols. The method is compatible with diverse acyl chlorides and complex drug-derived substrates, with stereocontrol arising from hydrogen-bonding in the transition state.

Synonyms: 2-(2,2,2-trifluoroethoxy)-1H-isoindole-1,3(2H)-dione; 2-(2,2,2-trifluoroethoxy)-2,3-dihydro-1H-isoindole-1,3-dione