Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

Carl J. Mallia¹, Paul M. Burton², Alexander M. R. Smith², Gary C. Walter², Ian R. Baxendale¹

• ¹ Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom
• ² Syngenta CP R&D Chemistry, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdom

A flow system to perform Chan–Lam coupling reactions of various amines and arylboronic acids has been realised employing molecular oxygen as an oxidant for the re-oxidation of the copper catalyst enabling a catalytic process. A tube-in-tube gas reactor has been used to simplify the delivery of the oxygen accelerating the optimisation phase and allowing easy access to elevated pressures. A small exemplification library of heteroaromatic products has been prepared and the process has been shown to be robust over extended reaction times.

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