36440-65-0Relevant academic research and scientific papers
C-H Activation under the Guise of Diels-Alder Reaction: Annulation toward the Synthesis of Benzo[e]isoindole-1,3-diones
Sheykhan, Mehdi,Shafiee-Pour, Maryam,Abbasnia, Masoumeh
, p. 1270 - 1273 (2017)
A new paradigm in the coupling of external alkenes with internal electron-deficient alkenes has been investigated in which an unprecedented annulation of vinylarenes on maleimides takes place. The reaction is carried out via a tandem in situ activation of both olefinic and aromatic C-H bonds of styrenes driving the reaction in a pseudo-Diels-Alder mode.
MOFs come up to scratch: An environmentally benign route to oxidative [4 + 2] cycloaddition on maleimides solely: Via MOFs in water
Abbasnia, Masoumeh,Bahmani, Mona,Sheykhan, Mehdi,Taghizadeh, Parvaneh
supporting information, p. 3216 - 3228 (2020/06/19)
The first Diels-Alder reaction of vinyl arenes with ene systems catalyzed by MOFs is reported. Maleimides and maleic anhydride were annulated/dehydrogenated on styrenes in the presence of a mixed-metal (FeNi)MIL-88A catalyst. Neither an additional oxidant nor a source of halogen is needed to drive this oxidative [4 + 2] cyclization reaction. Kinetic evidence such as activation entropy corroborates the proposed concerted mechanism. The reaction proceeds merely through a cost-effective catalyst in water as the greenest solvent. The product of annulation of styrene with maleic anhydride was used for the first L-selective annulative π-extension on naphthalene.
