Kinetically Controllable Pd-Catalyzed Decarboxylation Enabled [5 + 2] and [3 + 2] Cycloaddition toward Carbocycles Featuring Quaternary Carbons
Biwei Yan, Linhong Zuo, Xiaowei Chang, Teng Liu, Manying Cui, Yang Liu, Haiyu Sun, Weipeng Chen, Wusheng Guo
Abstract
A decarboxylative protocol has been developed toward a range of carbocycles. The key success is based on the use of a batch of newly designed cyclic carbonates as substrates that can provide carbon-carbon zwitterion intermediate under palladium catalysis. The kinetics of the reactions are controllable toward either strained seven- or thermodynamically more favored five-membered carbocycles. The release of this chemistry will shed light on the synthesis of complex and valuable cyclic structures.
Topics & Concepts
ChemistryZwitterionDecarboxylationCatalysisCycloadditionPalladiumCombinatorial chemistryCarbon fibersOrganic chemistryMoleculeMaterials scienceComposite numberComposite materialCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Alkyne Reactions