A novel ditopic ring-expanded N -heterocyclic carbene ligand-assisted Suzuki-Miyaura coupling reaction in aqueous media

Abstract A series of seven-membered ditopic ring-expanded N -heterocyclic carbene (dre-NHC) precursors, bearing sterically demanding and electron-rich aryl groups, were synthesised in moderate yields via the reaction of 1,2,4,5-tetrakis(bromomethyl)benzene with the corresponding N , N ′-diarylformamidines in the presence of K 2 CO 3 in acetonitrile under an air atmosphere. All new compounds were characterised by HRMS, NMR spectroscopy, and microanalysis, as well as X-ray crystallography for compound 1c . The development of an efficient catalytic system for the Suzuki-Miyaura coupling reaction of aryl chlorides with various boronic acids was also investigated using the in situ generated dre-NHC ligands.