Finalist EPFL doctorate Award 2013 - Jonathan Brand

© 2013 EPFL

© 2013 EPFL

Special distinction from the selection committee to Jonathan Brand for his thesis"Development of Catalytic Umpolung and Methodologies: Part 1: Direct Alkynylation of Heterocycles and Electron-Rich Aromatics using Alkynyl-Benziodoxolones. Part 2: Synthesis of New Bifunctional (Thio)urea Carbene Catalysts". Thesis No. 5397. Dir: Prof. Jérôme Waser

Organic chemistry has fundamentally impacted modern society; synthetic drugs have allowed tremendous progress in healthcare and organic materials are now an integral part of our life. Chemists are constantly challenged to develop efficient and environmental-friendly methods to access organic molecules.

Our research is focused on alkynes, molecules containing a triple bond between two carbon atoms, which are frequently used in the synthesis of bioactive compounds and in material science (mobile phone screens, solar cells…). We have discovered a new method using catalytic Umpolung to introduce alkynes directly onto aromatics -electron-rich molecules (indoles, pyrroles, furans, thiophenes, anisoles) omnipresent in drugs and materials. A novel concept in direct contrast to mainstream alkyne synthesis was implemented through the unique combination of an iodine-based reagent (TIPS-EBX) and gold catalysis. TIPS-EBX is now produced commercially by a world-leading chemical supplier and has already been used in industry. The method will be highly useful for the synthesis of drugs and materials.