Copper(II)-Mediated Intermolecular Radical [3+2]-Annulation of N,N-Dimethyl Enaminones: Direct Access to 5-Acyl-3-Furancarboxaldehydes

Copper(II)-mediated unprecedented intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed. The protocol is promoted simply by copper(II) chloride to access 5-acyl-3-furancarboxaldehydes with acceptable to good yields and broad substrate scope. This reaction allows the formation of multiple new bonds, including C(sp(2))-O bond between two nucleophilic sites, C(sp(2))-C(sp(2)) bond and C=O bond, through a radical cyclization process. Moreover, gram-synthesis and application research show the potential application value of this transformation in industry.

Automated summary

A copper(II)-mediated intermolecular radical [3+2] annulation of N,N-dimethyl enaminones has been developed, providing access to 5-acyl-3-furancarboxaldehydes with good yields and broad substrate scope. This reaction allows the formation of multiple new bonds through a radical cyclization process, showing potential application value in industry as demonstrated by gram-scale synthesis and application research.