A LIGHT ACTIVATED OLEFIN METATHESIS CATALYST EQUIPPED WITH A CHROMATIC ORTHOGONAL SELF-DESTRUCT FUNCTION

Revannath Sutar ^1,2 Efrat Levin ² Danielle Butilkov ² Israel Goldberg ³ Ofer Reany ¹ N. Gabriel Lemcoff ²

¹Department of Natural Sciences, The Open University of Israel
²Department of Chemistry, Ben-Gurion University of the Negev
³School of Chemistry, Tel Aviv University

A sulfur chelated photo-latent ruthenium olefin metathesis catalyst has been equipped with supersilyl groups on the N-heterocyclic carbene ligand. The silyl groups function as an irreversible chromatic kill switch, decomposing the catalyst on irradiation with 254 nm UV light. Thus, different types of olefin metathesis reactions may be started by irradiation with 350 nm UV light and prevented by irradiation with shorter wavelengths. The possibility to induce and impede catalysis just by using light of different frequencies opens the pathway for stereolithographic applications and novel light guided chemical sequences. Thus Complex light-guided chemical processes based on olefin metathesis, including polymerization, can be carried out by this protocol.

Figure 1:

Sutar, R. L.; Levin, E.; Butilkov, D.; Goldberg, I.; Reany, O.; Lemcoff, N. G., Angew. Chem. Int. Ed., 2015, DOI: 10.1002/anie.201508966R1