29621-69-0Relevant articles and documents
A new and effective method for providing optically active monosubstituted malononitriles: Selective reduction of α,β-unsaturated dinitriles catalyzed by copper hydride complexes
Ren, Yunlai,Xu, Xianlun,Sun, Kunpeng,Xu, Jian
, p. 4010 - 4014 (2005)
A copper hydride complex, which was generated in situ from CuOt-Bu, BINAP, and PhSiH3, was found to be a highly effective catalyst for the reduction of the CC of α,β-unsaturated dinitriles. In addition to CuOt-Bu, some air and moisture stable C
Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond
Chen, Xuanxiao,Gouverneur, Véronique,Hell, Sandrine M.,Meyer, Claudio F.,Ortalli, Sebastiano,Sap, Jeroen B. I.
, p. 12149 - 12155 (2021/09/28)
A process for the direct hydrofluoromethylation of alkenes is reported for the first time. This straighforward silyl radical-mediated reaction utilises CH2FI as a non-ozone depleting reagent, traditionally used in electrophilic, nucleophilic and carbene-type chemistry, but not as a CH2F radical source. By circumventing the challenges associated with the high reduction potential of CH2FI being closer to CH3I than CF3I, and harnessing instead the favourable bond dissociation energy of the C-I bond, we demonstrate that feedstock electron-deficient alkenes are converted into products resulting from net hydrofluoromethylation with the intervention of (Me3Si)3SiH under blue LED activation. This deceptively simple yet powerful methodology was extended to a range of (halo)methyl radical precursors including ICH2I, ICH2Br, ICH2Cl, and CHBr2F, as well as CH3I itself; this latter reagent therefore enables direct hydromethylation. This versatile chemistry was applied to18F-,13C-, and D-labelled reagents as well as complex biologically relevant alkenes, providing facile access to more than fifty products for applications in medicinal chemistry and positron emission tomography.
C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow
Deng, Yuchao,Fagnoni, Maurizio,Guthrie, Duncan,Laudadio, Gabriele,No?l, Timothy,Nun?, Manuel,Ravelli, Davide,Sun, Yuhan,Wal, Klaas Van Der
, p. 92 - 96 (2020/09/03)
Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp3)-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp3)-H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).