HAT Catalysts to Facilitate Acid Mediated Cleavage of Biaryl C-C Bonds in Binaphthols

Org Lett. 2022 Nov 18;24(45):8326-8330. doi: 10.1021/acs.orglett.2c03325. Epub 2022 Nov 7.

Abstract

A method to cleave the C-C biaryl bond of binaphthyl derivatives under reductive conditions is described. Triflic acid employed together with a catalytic HAT reagent, 2-ethyl-9,10-dihydroxyanthracene, that is regenerated using H2 with catalytic Pd/C yielded monomeric products in improved yields. A range of substrates is disclosed, and kinetic analyses provide insight into the mechanism of aryl-aryl activation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis*
  • Indicators and Reagents
  • Kinetics

Substances

  • Indicators and Reagents