Second PhD Project at TU Wien

PhD Project Title: Sustainable and safe C-H activation for large-scale production.

Principal Investigator: Prof. Michael Schnürch
https://www.ias.tuwien.ac.at/mdm/about-michael/

PhD Project description: The PhD student (ESR) will 1) develop a protocol for direct alkylation using quaternary ammonium salts under base-free conditions (reaction conditions effective in absence of base, or design of reactors allowing spatial separation); 2) design methylation reactions using, amongst others, non-toxic tetramethylammonium salts as a solid precursor of CH3 group; 3) elucidate the mechanism in collaboration with computational support from ESR3; 4) apply the method for isotope labeling (in particular 14C) of relevant compounds.

Preliminary results:

Description of the work: ESR6 will focus on further improving the alkylation reactions using quaternary ammonium salts previously published in the group.[1] In particular, basic conditions required for such transformation constitute an important drawback to be overcome (development of a protocol efficient under neutral conditions, spatial separation between different compartments of a reactor). ESR6 will also develop high yielding methylation reactions using, for example, tetramethyl-ammonium bromide as a solid precursor where initial results are promising and literature precedence with related reagents is available.[2] To illustrate the industrial perspectives of its IRP ESR6 will move to Boehringer to perform methylation on pharmaceutically relevant molecules. In parallel, ESR6 will explore the potential of C-H isotope labelling (introduction of 14C motifs) using N-14CH3-pyridinium salts.

Relevant skills that will be considered are:

  • Strong theoretical background and practical skills in organic synthesis and catalysis
  • Practical experience in analytical methods (NMR, MS, HPLC)
  • Good level of English proficiency (understood, spoken and written)
  • Skills in scientific writing (reports, papers, etc.)
  • Team spirit and collaborative predisposition

Planned secondments: “1 secondment (6 months) at Boehringer Ingelheim

[1] Spettel, M.; Pollice, R.; Schnürch, M. Org. Lett. 2017, 19, 4287

[2] a) Uemura, T.; Yamaguchi, M.; Chatani, N. Angew. Chem. Int. Ed., 2016, 55, 3162; b) den Hartog, T.; Sarria Toro, J. M.; Couzijn, E. P. A.; Chen, P. Chem. Commun. 2014, 50, 10604; c) Künzi, S. A.; Sarria Toro, J. M.; den Hartog, T.; Chen, P. Angew. Chem. Int. Ed., 2015, 54, 10670.

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