Construction of C–C Bond via C–N and C–O Cleavage

The construction of a C–C bond is a center subject in synthetic organic chemistry. The cross-electrophile coupling has provided a powerful tool to forge the C–C bond. However, this process generally requires organic halides, which has severely restricted the design space for new reactions. Herein, we highlight our recent work on the coupling reaction between C–N and C–O electrophiles. This work demonstrates the possibility of construction of C–C bond via C–N and C–O cleavage. A number of reactions between benzyl ammoniums and vinyl acetates, aryl ammoniums and vinyl acetates, and benzyl ammoniums and aryl C–O electrophiles have been studied. We also disclosed that benzyl ammonium salts can be activated by low-valent nickel to be radicals. 1 Introduction 2 Cross-Coupling of C–N and C–O Electrophiles 3 Summary and Outlook