Palladium catalyzed intramolecular alkenyl triflate-arene coupling: A C-H functionalization route to carbocycles

ORGN 140

Michael C. Willis, m.c.willis@bath.ac.uk and Ana Cruz, acfc20@bath.ac.uk. Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom
A novel catalytic method for using unfunctionalised aryl C-H bonds in palladium catalysed coupling reactions with vinyl triflates was developed. This strategy allows us to build new C-C bonds, starting with simple and readily available starting materials. The method developed employs a low catalyst loading (2-5 mol%) and mild temperatures.

We have shown that this is a general process and can be applied to a variety of substrates. The mechanism was investigated and a primary isotope effect was measured (kH/kD = 5.02). This suggests that the process follows a σ-bond methatesis pathway and not the more common electrophilic palladation mechanism.