56423-40-6Relevant articles and documents
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.
An effective cis-β-octahedral Mn(iii) SALPN catalyst for the Mukaiyama-Isayama hydration of α,β-unsaturated esters
Donnelly, Paul S.,North, Andrea J.,Radjah, Natalia Caren,Ricca, Michael,Robertson, Angus,White, Jonathan M.,Rizzacasa, Mark A.
supporting information, p. 7699 - 7702 (2019/07/09)
Two cis-β-MnIIISALPN catalysts were synthesised and tested in the Mukaiyama-Isayama hydration of α,β-unsaturated esters. The MnIIIEtOSALPN(acac) complex 7 is the most active and catalyses hydration with little or no detectable undesired alkene reduction. This catalyst is superior for alkene hydration compared to the originally reported Mn(dpm)3 catalyst.
Highly chemoselective hydrogenation method using novel finely dispersed palladium catalyst on silk-fibroin: Its preparation and activity
Ikawa, Takashi,Sajiki, Hironao,Hirota, Kosaku
, p. 2217 - 2231 (2007/10/03)
A palladium-fibroin complex (Pd/Fib) was prepared by soaking silk-fibroin in MeOH solution of Pd(OAc)2 for 2 days (under Ar atmosphere) - 4 days (under air). Pd(OAc)2 was gradually absorbed by fibroin and the rapid reduction of fibroin conjugated Pd(OAc)2 proceeded with MeOH as a reductant at room temperature to be the Pd(0) complex. Pd/Fib catalyzed chemoselective hydrogenation of acetylenes, olefins and azides in the presence of aromatic ketones and aldehydes, halides, N-Cbz protective groups and benzyl esters which are readily hydrogenated using Pd/C or Pd/C(en) as a catalyst.