Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands

An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.

Automated summary

An efficient and straightforward method has been developed to synthesize heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. This method offers a simple way to produce QUINOX and related compounds with high site selectivity, and the synthesized naphthols can be transformed into privileged ligands. Suitable resolution methods can directly provide axially chiral heterobiaryls.