Cu(II)/Vasicine Promoted Intramolecular C-O Formation: Synthesis of Benzoxazoles in EtOH

Abstract

Aims and objectives: Benzoxazoles are valuable bicyclic aromatic compounds; the construction of benzoxazoles via C-O cross-coupling reactions has attracted more and more attention.

Materials and methods: The best condition of C-O bond formation from o-haloanilides was carried out, taking Cu(OTf)₂ (5 mol%) and vasicine (10 mol%) as the catalysts in EtOH in the presence of K₂CO₃ (2 eq.) for 12 h at 90°C.

Results: A series of 2-substituted benzoxazoles have been prepared in high yields from 2-bromoanilides and 2- iodioanilides under mild conditions.

Conclusion: We have developed an efficient Cu-vasicine catalytic system for intramolecular C-O bond formation. This strategy is applicable to the synthesis of a wide variety of 2-substituted benzoxazoles by intramolecular O-arylation of o-haloanilides.

Keywords: Cu(II)-vasicine; EtOH; benzoxazoles; cross-coupling reactions; intramolecular O-arylation; o-haloanilides.