Organic Chemistry, Short Talk
OC-026

Designing Electric-Field Catalysis Systems For Monoterpene Cyclizations

A. Jozeliūnaitė1, S. Guo1*, N. Sakai1*, S. Matile1*
1Department of Organic Chemistry, University of Geneva, Swtizerland

Essentially, all chemical reactions can be viewed as the movement of electrons. In theory, by precisely aligning oriented external electric fields (OEEFs) along the reacting species to direct this movement, it provides control over both the reactivity and selectivity of non-redox reactions. Despite the theoretical promises, the practical application of electric-field catalysis has primarily been restricted to unconventional conditions, such as designed local electric field-based (dLEFs) systems, single molecules on STM tips, or reactions in water droplets. Thus, the transition to scalable organic synthesis poses challenges that must be addressed to develop broadly applicable electric-field catalysis methods.

To contribute to these efforts, we became interested in the development of monoterpene cyclizations initiated by OEEFs.1 This was accomplished by utilizing an electrochemical microfluidic reactor equipped with a graphite electrode coated with easily polarizable multiwalled carbon nanotubes (MWCNTs).1,2 Depending on the orientation of the applied electric field, MWCNTs generated strong local macrodipoles, catalyzing cyclization on the surface through interactions with anionic or cationic parts of reactive intermediates. Going forward, our aim is to broaden the scope of electric-field-controlled transformations by tuning system design to enable catalysis at high electric fields.

[1] A. Jozeliunaite, S.-Y. Guo, N. Sakai, S. Matile, Angew. Chem. Int. Ed. 2025, 64, e202417333

[2] M. Á. Gutiérrez López, R. Ali, M.-L. Tan, N. Sakai, T. Wirth, S. Matile, Sci. Adv. 2023, 9, eadj5502