50782-89-3Relevant academic research and scientific papers
Benzyl radicals from toluene by photosensitization with naphthalene-1,4- dicarbonitrile - Benzylation and hydroxymethylation of unsaturated compounds
Mella, Mariella,Fagnoni, Maurizio,Albini, Angelo
, p. 2137 - 2142 (2007/10/03)
In aprotic media, photoinduced electron transfer from toluene to 1,4- naphthalenedicarbonitrile (DCN) is followed by in-cage proton transfer and radical coupling. However, in the presence of a protic co-solvent, the radical ions diffuse out of the cage and deprotonation of the toluene radical cation takes place from the free solvated species. With (BuOH, this results in reductive benzylation of DCN through coupling of benzyl radicals with DCN-·. With MeOH, secondary hydrogen abstraction by PhCH2- yields hydroxymethyl radicals, which couple with DCN-·. Both benzyl and hydroxymethyl radicals are efficiently trapped by electrophilic alkenes. Thus, in the presence of dimethyl maleate, DCN-photosensitized benzylation - or hydroxy-methylation - of the substrate occurs through direct activation of the C-H bond. The same reaction has been accomplished with acrylonitrile, albeit with a lower yield.
Hydroxyalkylation and Lactone Formation from Dialkyl Malonate by Means of a EuIII/EuII Photoredox System
Ishida, Akito,Yamashita, Shinya,Takamuku, Setsuo
, p. 2229 - 2231 (2007/10/02)
A EuIII/EuII photoredox system in alcohol induced an effective hydroxyalkylation at an α-position of a dialkyl malonate.The alcohol adduct was then converted to the lactone.A step-by-step hydroxyalkylation mechanism was suggested in which the Eu ion is used as a photocatalyst and also as a condensation catalyst for the reaction of dialkyl malonates and aldehydes.
