Aryl Dance Reaction of Arylbenzoheteroles

Org Lett. 2022 Nov 4;24(43):8083-8087. doi: 10.1021/acs.orglett.2c03442. Epub 2022 Oct 26.

Abstract

We report a 1,2-migration (aryl dance reaction) of the aryl group on heteroles. AlCl3 can efficiently convert C3-arylheteroles to C2-arylheteroles. Depending on the electron density of the substrate, conversion from C2- to C3-arylheteroles was also possible with catalytic Zn(OTf)2. A one-pot aryl dance/acylation or bromination and arylation/aryl dance cascade was also demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Catalysis
  • Dancing*
  • Molecular Structure

Substances

  • zinc trifluoromethanesulfonate