Department of Chemistry

Department of Chemistry University of Oxford

First paper from the UCB-Oxford Late Stage Functionalisation Group appears online

First paper from the UCB-Oxford Late Stage Functionalisation Group appears online

The Late Stage Functionalisation Project, a collaboration between UCB BioPharma and Oxford, has published its first paper “C–H Cyanation of 6-Ring N-Containing Heteroaromatics” in Chemistry – A European Journal. The transformation is achieved through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, and is shown to be effective in the presence of sensitive functional groups, and across a range of substitution patterns. It has been applied to the late stage functionalisation of several complex drugs, demonstrating its great potential utility for medicinal chemists. Computational studies have shown that site selectivity can be easily predicted through the use of Fukui indices, aiding the application of the methodology to complex substrates. more........