Expanded ring N-heterocyclic carbenes: A comparative study of ring size in palladium (0) catalysed Mizoroki–Heck coupling

Abstract

The synthesis and characterisation of a range of new 6- and 7-membered expanded ring N-heterocyclic carbene (NHC) complexes of zero valent palladium dvtms (divinyltetramethyldisiloxane) 8–14 is reported, with the first comparative catalytic study probing the effects of large ring N-heterocyclic carbene ligands (6-Mes and 7-Mes) with their analogous 5-membered derivative (IMes) on catalytic performance. The catalytic performances of the [Pd(NHC)(dvtms)] complexes are evaluated in the Mizoroki–Heck coupling of 4-bromoacetophenone and n-butyl acrylate, providing a ready and effective comparison into the influence of ring size and steric congestion on catalytic activity in carbon–carbon cross coupling reactions.