Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (<i>E</i>)-Stilbenes and (1<i>E</i>,3<i>E</i>)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
Zhao Zhang, Dejiang Zhang, Longzhi Zhu, Dishu Zeng, Nobuaki Kambe, Renhua Qiu
Abstract
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
Topics & Concepts
ChemistryYield (engineering)ResveratrolReagentQuantum yieldCatalysisSelectivityFluorescenceCoupling (piping)Medicinal chemistryPalladiumCombinatorial chemistryOrganic chemistryPhysicsBiochemistryQuantum mechanicsMechanical engineeringEngineeringThermodynamicsCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions