832-66-6Relevant articles and documents
Profiling the oxidative activation of DMSO-F6 by pulse radiolysis and translational potential for radical C-H trifluoromethylation
Santschi, Nico,Jelier, Benson J.,St?helin, Samuel,Nauser, Thomas
supporting information, p. 9734 - 9742 (2019/12/02)
The oxidative activation of the perfluorinated analogue of dimethyl sulfoxide, DMSO-F6, by hydroxyl radicals efficiently produces trifluoromethyl radicals based on pulse radiolysis, laboratory scale experiments, and comparison of rates of reaction for analogous radical systems. In comparison to commercially available precursors, DMSO-F6 proved to be more stable, easier to handle and overall more convenient than leading F3C-reagents and may therefore be an ideal surrogate to study F3C radicals for time-resolved kinetics studies. In addition, we present an improved protocol for the preparation of this largely unexplored reagent.
Late-stage functionalization of biologically active heterocycles through photoredox catalysis
DiRocco, Daniel A.,Dykstra, Kevin,Krska, Shane,Vachal, Petr,Conway, Donald V.,Tudge, Matthew
supporting information, p. 4802 - 4806 (2014/05/20)
The direct C-H functionalization of heterocycles has become an increasingly valuable tool in modern drug discovery. However, the introduction of small alkyl groups, such as methyl, by this method has not been realized in the context of complex molecule synthesis since existing methods rely on the use of strong oxidants and elevated temperatures to generate the requisite radical species. Herein, we report the use of stable organic peroxides activated by visible-light photoredox catalysis to achieve the direct methyl-, ethyl-, and cyclopropylation of a variety of biologically active heterocycles. The simple protocol, mild reaction conditions, and unique tolerability of this method make it an important tool for drug discovery.
ADDITION OF ELECTROPHILIC RADICALS TO CAFFEINE: SYNTHETIC ASPECTS AND INFLUENCE OF THE PEROXIDIC INITIATORS
Zylber, J.,Ouazzani-Chahdi, L.,Lefort, D.,Chiaroni, A.,Riche, C.
, p. 721 - 732 (2007/10/02)
Primary and secondary electrophilic radicals such as: .CHRCO2CH3 (R=H, CH3, CO2CH3) and tertiary .CCl3 radical were added directly at C-8 of, th model purine compound, caffeine to give the corresponding 8-substituted derivatives in fairly good yields.Unexpected reaction of caffeine with oxy radicals from the initiators (PhCO2., t-BuOO.) gave rise to C-5 substituted 1,3,7-trimethyl-5,7-dihydrouric acid derivatives (C-5-R=CCl3, CH3, C(CH3)2CO2CH3) and to the spirodihydantoin C-8 adduct derivative of caffeine 11.