(tert-Butoxy)carbonyl-(2,2,2-trifluoroethyl)amino 4-(trifluoromethyl)benzoate

CAS 2760510-18-5, Cat. No EN300-55516482
Reagent for aminofluoroalkylation

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This N-trifluoroethyl hydroxylamine derivative is a photoredox-active radical precursor used for the installation of the α-trifluoromethylamine motif (similar reagent EN300-56428309). Upon single-electron reduction, cleavage of the N–O bond generates an N-centered Boc-protected trifluoroethyl radical, which readily undergoes a 1,2-hydrogen atom transfer (1,2-HAT) to form the more stable carbon-centered •CH(NHBoc)CF₃ radical. In visible-light trifluoroethylamination, this radical reacts with quinoxalin-2(1H)-ones, providing α-trifluoromethylamine derivatives under mild conditions with broad tolerance toward alkyl, benzyl, allyl and propargyl substituents as well as F, Cl, Br, ester, methoxy, methyl, CN and nitro functionalities¹. Moreover, there is a methodology for efficient photoredox catalytic C_α radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes and reagent that results in the gem-difluoroallylated α-trifluoromethylamines². In a complementary three-component photoredox process, the reagent reacts with styrenes and DMSO to furnish medicinally relevant β-trifluoromethyl β-amino ketones³; para-, meta- and ortho-substituted styrenes as well as complex derivatives of ibuprofen, bicyclopentane and carbohydrates are tolerated, whereas nonaromatic alkenes, pyridyl alkenes and styrenes bearing strongly electron-withdrawing CF₃, CHO or CO₂H groups are ineffective. More recently, the same reagent was employed in Ni/photoredox cross-coupling with aryl bromides under continuous-flow conditions⁴, directly installing the Ar–CH(NHBoc)CF₃ unit with up to 84% yield across 32 examples; esters, ketones, aldehydes, nitriles, chlorides, sulfones, alkenes and heteroaryl bromides are tolerated, while aryl iodides also react and aryl chlorides are substantially less effective. Overall, the reagent is a versatile masked α-aminotrifluoroethyl radical source for C–C bond formation, enabling trifluoroethylamination, alkene difunctionalization and transition-metal-mediated arylation to access diverse α- and β-CF₃ amine architectures.

Synonyms: [(1,1-dimethylethoxy)carbonyl](2,2,2-trifluoroethyl)azanyl 4-(trifluoromethyl)benzoate; tert-butyl (2,2,2-trifluoroethyl)((4-(trifluoromethyl)benzoyl)oxy)carbamate; [(tert-butoxy)carbonyl](2,2,2-trifluoroethyl)amino 4-(trifluoromethyl)benzoate