Development of an orthogonal, stereodivergent synthesis machinery programmable by light

• Applicant: Dr. Niklas Thiel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2020 to 2021
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 441238206

In this research project, a photoswitchable catalytic system capable of catalyzing orthogonal reactions is presented. The system features a molecular motor core bearing oxazoline- and phosphine-based coordination sites for transition metal complexation. The resulting ligand comprises a bis(oxazoline) or phosphinooxazoline ligand framework, depending on the switching state. Upon light irradiation, a large geometrical change (photochemical E/Z-isomerization) induces the switching between the two states. This concept of switching the ligand type (N,N- to P,N-ligand and vice-versa) will be utilized in chemical transformations such as the Heck reaction, cyclopropanations, and Diels-Alder reactions. The unique feature of molecular motors, having four selectively addressable states (two “pseudo” enantiomers of each ligand framework), enables switching enantioselectivity on top of the orthogonality. Thus rendering the system a programmable stereodivergent machinery. Furthermore the viability in sequential reactions of this type will be investigated.

• DFG Programme: Research Fellowships
• International Connection: Netherlands
• Host: Professor Dr. Ben L. Feringa