Final Report Summary - CHACT_RHAZ (Metal catalysed C-H bond activation strategies for chemical synthesis & cancer biology)
Over the past decade, there has been much attention on C-H arylation of arenes since the product biaryl unit is frequently found in many important biologically interesting compounds, pharmaceutical reagents and functional polymers. However, these processes have been limited to the functionalisation of a C-H bond adjacent to a directing group (ortho C-H functionalisation). Clearly, full potential can only be realised when other positions of arene ring can be arylated.
The researcher has successfully developed a novel site-selective C-H bond functionalisation process employing inexpensive copper catalysts. The use of hypervalent iodine compounds allows arylation to occur at the meta C-H bond relative to a carbonyl directing group. This exquisite regiocontrol allows access to a variety of interesting compounds that are not easy to obtain via traditional chemistry. In particular, the methodology facilitates facile conversion of drug molecules, such as ibuprofen, into biaryl analogues for further biological studies. The researcher also discovered a condition for metal-free C-H arylation. This finding offers exciting potentials for further developments since it avoids the use of metal catalyst, which in many cases is difficult to separate from products and affects the quality of the desired materials.