Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams

A visible-light photoredox-catalyzed reductive alpha-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of alpha,alpha-disubstituted gamma-amino acids and gamma-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin a-aminomethyl carboxylation. These findings not only provide new access to alpha,alpha-disubstituted gamma-amino acids and gamma-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

Automated summary

A visible-light photoredox-catalyzed reductive alpha-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed, resulting in the synthesis of a series of alpha,alpha-disubstituted gamma-amino acids and gamma-lactams with high efficiency and regioselectivity. This process not only provides new access to these compounds but also demonstrates the concept of CO2 reutilization in decarboxylation reactions.