Photocatalytic Synthesis of Substituted Cyclic Carbonate Monomers for Ring-Opening Polymerization

An operationally mild, ruthenium-based photocatalytic protocol has been developed for the conversion of gamma-mono- and gamma,gamma-disubstituted allyl carbonates in the presence of Umemoto's reagent to afford substituted six-membered cyclic carbonates. Variation and diversification of the carbonate ring substitution provides access to new monomers useful in ring-opening polymerization leading to polycarbonates with potentially tailored properties, as illustrated by comparative experiments using monomers with different pi-stacking capabilities.

Automated summary

An operationally mild, ruthenium-based photocatalytic protocol has been developed for the conversion of gamma-mono- and gamma,gamma-disubstituted allyl carbonates to substituted six-membered cyclic carbonates. The variation and diversification of carbonate ring substitution provides access to new monomers useful in ring-opening polymerization, leading to polycarbonates with potentially tailored properties.