ThioCORMates: Tunable and Cost-Effective Carbon Monoxide-Releasing Molecules

Abstract

Carbon monoxide-releasing molecules (CORMs) can offer a safer alternative to CO delivery than the use of CO gas cylinders. Upon treatment with an amine base, S-aryl thioformates ("thioCORMates") release CO nearly quantitatively at room temperature, a gas which can then be harnessed for carbonylative cross-coupling, biological study, or inorganic synthesis. These bench-stable molecules are easily synthesized from the corresponding thiophenol and can be electronically tuned to release CO at different rates-from less than 1 min to greater than 1 h-offering a practical alternative to existing CORM technology. Finally, isotopically labeled ¹³ CO can be conveniently generated and used, with the thioCORMate synthesized from ¹³ C-formic acid.

Keywords: carbonyl ligands; carbonylation; cross-coupling; heme proteins.