Photocatalyzed <i>E</i>→<i>Z</i> Contra‐thermodynamic Isomerization of Vinyl Boronates with Binaphthol
Thibaud Brégent, Jean‐Philippe Bouillon, Thomas Poisson
Abstract
The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.
Topics & Concepts
IsomerizationChromophoreCatalysisChemistryPhotochemistryComputational chemistryMaterials scienceOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques