Kinetically Controllable Pd-Catalyzed Decarboxylation Enabled [5+2] and [3+2] Cycloaddition toward Carbocycles Featuring Quaternary Carbons

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.

Automated summary

A decarboxylative protocol using cyclic carbonates as substrates has been developed to synthesize carbocycles, with controllable kinetics towards strained seven- or more thermodynamically favored five-membered rings. The release of this chemistry will benefit the synthesis of complex and valuable cyclic structures.