CCVC Seminar: Dr. Jan-Erling Bäckvall: Biomimetic Catalysis in Green Organic Transformations

Carbocyclizations, annulation processes involving carbon-carbon bond formation via carbometalation, constitute an extremely important and useful class of reaction for the syntheses of carbocyclic and heterocyclic compounds. We have recently developed a number of selective palladium-catalyzed oxidative carbocyclizations of unsaturated systems often involving the use of molecular oxygen as the oxidant in a biomimetic approach. Mild oxidative C-C bond formation under aerobic conditions can be achieved via this approach.

We have developed oxidative borylative and arylative carbocyclization of en­allenes, allenynes, and bis-allenes as well as  C-H activation/carbocyclization of arylallenes. For some recent applications see ref 1-5.

In another approach to biomimetic catalysis, enzymes have been combined with racemization catalysts for dynamic kinetic resolution.6 An example of the latter approach is the development of a biomimetic hybrid catalyst that works as an artificial metalloenzyme.7

1. T. Jiang, T. Bartholomeyzik, J. Mazuela, J. Willersinn, and J. E. Bäckvall, Angew. Chem. Int. Ed. 2015, 54, 6024–6027.

2. C. Zhu, B. Yang, T. Jiang, and J. E. Bäckvall, Angew. Chem. Int Ed. 2015, 54, 9066-9069.

3. J. Mazuela, D. Banerjee, and J. E. Bäckvall, J. Am. Chem. Soc. 2015, 137, 9559-9562.

4. C. Zhu, B. Yang, and J. E. Bäckvall, J. Am.Chem. Soc. 2015, 137, 11868–11871.

5. Y. Qiu, B. Yang, C. Zhu, and J.-E. Bäckvall, Angew. Chem. Int Ed. 2016, 55,  6520-6524.

6. O. Verho and J. E. Bäckvall J. Am.Chem. Soc. 2015, 137, 3996–4009.

7. K. Engström, E. V. Johnston, O. Verho, K. Gustafson, M. Shakeri, C.-W. Tai, and J. E. Bäckvall, Angew. Chem. Int. Ed. 2013, 52, 14006–14010.