Flow carbonylation of sterically hindered ortho-substituted iodoarenes

Beilstein J Org Chem. 2016 Jul 19:12:1503-11. doi: 10.3762/bjoc.12.147. eCollection 2016.

Abstract

The flow synthesis of ortho-substituted carboxylic acids, using carbon monoxide gas, has been studied for a number of substrates. The optimised conditions make use of a simple catalyst system compromising of triphenylphosphine as the ligand and palladium acetate as the pre-catalyst. Carbon monoxide was introduced via a reverse "tube-in-tube" flow reactor at elevated pressures to give yields of carboxylated products that are much higher than those obtained under normal batch conditions.

Keywords: carbon monoxide; carbonylation of ortho-substituted substrates; flow chemistry; gases in flow; “tube-in-tube”.