Radical Conjugate Addition of Acylsilane Enabled by Synergistic Photoredox and Lewis Acid Catalysis
Ning Guo, Yao Luo, Lili Feng, Zhili Liu, Weidi Cao, Xiaoming Feng
Abstract
Abstract A visible‐light‐induced acyl radical conjugate addition to electron‐deficient alkenes with acylsilane was realized by merging photoredox and Lewis acid catalysis under mild reaction conditions. Various tri‐ and tetra‐substituted furans were obtained with good yield (up to 97%) from α,β‐unsaturated ketones. Based on the experimental results and spectral analysis, a possible catalytic cycle involving 1,4‐conjugate addition/ring‐closure/arylation sequence was proposed. Beyond that, 1,6‐acyl radical conjugate addition to para ‐quinone methides was also accomplished to deliver a series of α‐aryl ketones by using this synergistic catalysis protocol.
Topics & Concepts
ChemistryPhotoredox catalysisConjugateLewis acids and basesCatalysisLewis acid catalysisPhotochemistryCatalytic cycleYield (engineering)Chiral Lewis acidAcid catalysisOrganic chemistryCombinatorial chemistryMedicinal chemistryPhotocatalysisMathematical analysisMathematicsMaterials scienceMetallurgyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods