Formal dual C(sp2)-H cross-dehydrogenative C-O bond formation to construct highly functionalized diaryl ethers with O2

A formal dual C(sp(2))-H cross-dehydrogenative C-O bond formation between phenols and N-substituted naphthylamines to expediently assemble diversely functionalized diaryl ethers bearing hydroxyl and amino functionalities with excellent atom and step economy was developed under mild conditions. The reaction features three C-H cleavages and three C-O bond formations in one pot. In addition a rare C(sp(2))-O bond formation rather than the conventional C-C bond formation took place by addition to a carbonyl O atom of the in situ generated ortho-quinone.

Automated summary

A formal dual C(sp(2))-H cross-dehydrogenative C-O bond formation method was developed, which can efficiently assemble diversely functionalized diaryl ethers. The reaction proceeds under mild conditions with excellent atom and step economy. In addition, a rare C(sp(2))-O bond formation occurs in this reaction.