CAS 3074458-35-5, Cat. No EN300-56428309
Reagent for aminofluoroalkylation
The reagent is a redox-active N-(2,2-difluoroethyl)hydroxylamine derivative (like EN300-55516482) that serves as a versatile aminofluoralkyl motif precursor for the synthesis of fluorinated nitrogen-containing compounds. Upon photoinduced single-electron reduction, it undergoes N–O bond cleavage followed by intramolecular 1,2-hydrogen atom transfer (1,2-HAT), generating a carbon-centered radical that enables the introduction of the –CH(NHBoc)–CHF₂ fragment into organic molecules. In organophotoredox-catalyzed three-component reactions with styrenes and DMSO, the reagent provides β-difluoromethyl β-amino ketones in moderate yields under mild conditions using 4DPAIPN and visible light1. In a complementary photoinduced Pd-catalyzed Heck-type aminoalkylation of alkenes2, it enables the synthesis of α-difluoromethyl allylamines. The broader methodologies demonstrate compatibility with substituted styrenes, heteroaromatic substrates, and structurally complex molecules, offering opportunities for late-stage functionalization.
Synonyms: benzoic acid, 4-(trifluoromethyl)-, (2,2-difluoroethyl)[(1,1-dimethylethoxy)carbonyl]azanyl ester; (tert-butoxy)carbonyl(2,2-difluoroethyl)amino 4-(trifluoromethyl)benzoate; [(tert-butoxy)carbonyl](2,2-difluoroethyl)amino 4-(trifluoromethyl)benzoate
Selected publications
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Direct Assembly of Privileged α-CF3 Allylamines via Photoinduced Pd-Catalyzed C–H Aminoalkylation of Alkenes.
Zhou, J.; Hu, L. P.; Fan, X.; Shen, P. H.; Xu, J.; Xu, H. J. Org. Lett. 2025, 27 (48), 13380–13386. DOI: 10.1021/acs.orglett.5c04528
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Organophotoredox-Driven Three-Component Synthesis of β-Trifluoromethyl β-Amino Ketones.
Gil-Ordóñez, M.; Gallego-Gamo, A.; Sarró, P.; Pleixats, R.; Gimbert-Suriñach, C.; Vallribera, A.; Granados, A. Journal of Organic Chemistry 2025, 90 (6), 2500–2509. DOI: 10.1021/acs.joc.4c03142