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

Beilstein J Org Chem. 2016 Jul 26:12:1598-607. doi: 10.3762/bjoc.12.156. eCollection 2016.

Abstract

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.

Keywords: Chan–Lam coupling; flow chemistry; gases in flow; oxygen; “tube-in-tube”.