Catalytic Reversible (De)hydrogenation To Rotate a Chemically Fueled Molecular Switch

Angew Chem Int Ed Engl. 2022 Dec 12;61(50):e202214763. doi: 10.1002/anie.202214763. Epub 2022 Nov 15.

Abstract

We report here the development of a rotating molecular switch based on metal-catalyzed reversible (de)-hydrogenation. Under an argon atmosphere, acceptorless dehydrogenation induces a switch from an alcohol to a ketone, while reversing to a hydrogen pressure switches back the system to the alcohol. Based on a tolane scaffold, such reversible (de)-hydrogenation enables 180° rotation. The absence of waste accumulation in a switch relying on chemical stimuli is of great significance and could potentially be applied to the design of efficient complex molecular machines.

Keywords: Catalysis; Conformation; Green Chemistry; Hydrogenation; Molecular Switch.