59919-11-8Relevant articles and documents
Visible light mediated reductions of ethers, amines and sulfides
Monos, Timothy M.,Magallanes, Gabriel,Sebren, Leanne J.,Stephenson, Corey R.J.
, p. 240 - 248 (2016/07/21)
Visible light-mediated photoredox catalysis enables the chemoselective reduction of activated carbon–heteroatom bonds as a function of reduction potential. The expansion of the scope of C–X bond reductions towards less activated motifs, such as ethers, amines and sulfides, is important to both organic synthesis and macromolecular degradation method development. In the present report, exploration of photoredox catalysis in alcoholic solvents mediated a decrease in the super-stoichiometric use of iPr2NEt and HCO2H in the reduction of α-keto ethers, amines and sulfides. Additionally, in the absence of fragmentation, [Formula presented] bond formation was afforded, suggesting an intermediate ketyl radicals are present in these transformations.
Thiophenol-Promoted Radical Chain Reduction of α-Substituted Isobutyrophenones by 1,3-Dimethyl-2-phenylbenzimidazoline
Tanner, Dennis D.,Chen, Jian Jeffrey
, p. 662 - 666 (2007/10/02)
The reduction of α-haloacetophenones and α-halopropiophenones by 1,3-dimethyl-2-phenylbenzimidazoline (DMBI) have been reported to proceed via an electron-transfer free-radical chain mechanism.The reduction of α-haloisobutyrophenones did not proceed by the chain sequence.We mow report that initiated reductions of α-bromo- and α-chloroisobutyrophenones (IIIa,b) have been found to be promoted by the addition of thiophenol.Isobutyrophenone was formed as the major product via a free-radical chain process.During the PhSH-promoted DMBI reduction of IIIa,b a minor product, α-(phenylthio)isobutyrophenone (IV), was also formed via nucleophilic substitution.The chain propagation steps involve the efficient hydrogen atom transfers between PhCOCMe2. and PhSH and between PhS. and DMBI.The facile hydrogen transfer between PhS. and DMBI was comfirmed by carrying out the radical-chain reduction of PhSSPh with DMBI.
Reactions of Nucleophiles with α-Halo Ketones
Russell, Glen A.,Ros, Francisco
, p. 7349 - 7351 (2007/10/02)
-