TBADT-Mediated C-C Bond Formation Exploiting Aryl Aldehydes in a Photochemical Flow Reactor

• Adam Cruise^a
• Marcus Baumann^a

• ^aUniversity College Dublin, School Of Chemistry, Science Centre - South, Dublin 4 Belfield, IRELAND

A robust and general photochemical process is reported converting various aryl aldehydes into β-ketonitriles and related species. Tetrabutylammonium decatungstate (TBADT) is used as photocatalyst in combination with a high-power LED emitting at 365 nm. Standardization and scalability are enabled by using a flow reactor platform integrating the LED light source placed within an encased reactor coil. Under optimized conditions a variety of aromatic and heteroaromatic aldehydes is reacted with acrylonitrile, methyl methacrylate and phenyl vinyl sulfone to give the desired products in high yields, short residence times of 5-30 minutes and a throughput of up to 41 mmol/h. This continuous process overcomes limitations previously encountered for aromatic substrates and represents an effective means to generate a variety of difunctionalized building blocks for further elaborations with an ideal atom economy.

Read the publication that featured this abstract