RT info:eu-repo/semantics/article
T1 Effect of Reaction Media on Photosensitized [2+2]- Cycloaddition of Cinnamates
A1 Abramov, Alex
A1 Reiser, Oliver
A1 Díaz Díaz, David
K1 [2+2]-cycloadditions
K1 photosensitizers
K1 supramolecular gels
K1 diradicals
K1 diastereoselectivity
K1 photocatalysis
K1 [2+2]-cicloadiciones
K1 fotosensibilizadores
K1 geles supramoleculares
K1 fotocatálisis
AB The outcome of photosensitized [2+2]-cycloaddition reactionsof various cinnamates has been compared in different reactionmedia, including homogeneous organic solutions under inertconditions, degassed water, and aerated physical gels. Thereactions were performed under LED blue light (λmax=455 nm)irradiation and [Ir{dF(CF3)ppy}2(dtb-bpy)]PF6 (1.0 mol%) as photocatalyst.The processes were optimized taking into considerationsolvent, gelator, and substrate. Comparative kineticsanalyses, as well as the effect of the reaction media on thediastereoselectivity of the process, were evaluated during thisinvestigation. In a number of cases, carrying out the reaction ina less polar solvent, like toluene or highly polar solvent, likewater had a tremendous impact on the diastereoselectivity ofthe process, pointing towards an effect on the stabilization ofthe putative diradical intermediate in this medium. Moreover,while for reactions run in homogeneous solution oxygen needsto be excluded, no erosion in yield is observed when thephotoadditions were run in aerated gel media.
PB Wiley
YR 2020
FD 2020
LK http://riull.ull.es/xmlui/handle/915/21327
UL http://riull.ull.es/xmlui/handle/915/21327
LA en
NO Deutsche Forschungsgemeinschaft
DS Repositorio institucional de la Universidad de La Laguna
RD 02-may-2024