Synthetic Chemistry of CO-RetainingMolecules

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Carbon monoxide (CO) plays a central role in carbonylation chemistry, however, the toxicity and the necessity of cautious handling have often prevented chemists to use CO for ordinary organic synthesis. In this study we focused on the use of potential CO retaining molecules for carbonylation reactions in the hope of providing useful carbonylation methods. The Morgan reaction comprising formic acids and sulfuric acid was examined in a gas permeable PTFE tube to generate CO, showing that acids stayed inside the tube and only CO gas came out from the tube. Flow carbonylation reaction system was created using a tube in tube system composed of an outer stainless-steel tube and an inner PTFE tube. In the outer tube, Pd-catalyzed carbonylation reaction took place to give the amide. In the presence of NHC・borane, hydroxymethylation of iodobenzene using CO was investigated under photo-irradiation conditions.