Education

• Postdoctoral Fellow, University of Tokyo
• Ph.D., Max-Planck Institut für Kohlenforschung/University of Cologne
• M.Sc., Chemistry, LMU Munich
• B.S., Chemistry & Biochemistry, LMU Munich

Awards/Honors

2023 - Kakenhi Early-Career Grant
2018 - MilliporeSigma Alfred Bader Award 1st Prize 
2018 - European Young Chemist Award Gold Medal

Research Interests

Synthetic organic chemistry, asymmetric catalysis, organofluorine chemistry, sulfur-fluorine compounds and materials, transition metal catalyzed cross-coupling reactions, medicinal chemistry.

Current Research

Our group’s research is defined along three major objectives around the theme of organofluorine chemistry for the 21^st century:

1. Expanding the chemical space for sulfur-(fluorine) functional groups in medicinal chemistry.
2. Mitigating the PFAS problem through novel degradation technology & development of PFAS alternatives.
3. Introducing novel concepts for high-performance catalysis in cross-coupling reactions and asymmetric synthesis.

Recently, we have developed a generalized synthetic approach toward aryl– and heteroaryl pentafluorosulfanyl (SF₅) compounds from various common building blocks through a two-step thiolation cross-coupling, oxidative fluorination strategy. The pentafluorosulfanyl group (SF₅) is widely regarded as a "super-trifluoromethyl" group (CF₃) and features an increased size, electronegativity and lipophilicity resulting in enhanced molecular characteristics. The introduction of SF₅ groups frequently enhances efficacies for pharmaceuticals and crop protection agents, yet synthetic access has been limited. In continuation of this work, we have expanded our approach to a divergent synthetic strategy for accessing the family sulfur-containing functional groups (SFGs) from (hetero)aryl trityl sulfides (ArSCPh₃) as the common precursors. Important sulfur motifs include aryl tetrafluoro-λ⁶-sulfanyl chlorides (ArSF₄Cl), aryl sulfonimidoyl fluorides (ArS(O)(NR)F), aryl sulfonyl fluorides (ArSO₂F), aryl sulfonic acids (ArSO₃H), and aryl sulfinyl fluorides (ArSOF), all of which are viable modifications in modern drug development. 

Selected Publications

(1) L. Yue, T. Okazoe T. Gatzenmeier*, K. Nozaki* “Pd-Catalyzed Thiotritylation Cross-Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups” ChemistryEurope 2024, 2, e202400053.

(2) T. Gatzenmeier*, L. Yue, M. Akamatsu, T. Okazoe, K. Nozaki* “Straightforward pentafluorosulfanylation for molecular design” 2023, ChemRxiv. https://doi.org/10.26434/chemrxiv-2023-jzn11.

(3) T. Gatzenmeier, M. Turberg, D. Yepes, Y. Xie, F. Neese, G. Bistoni, B. List “A Scalable and Highly Diastereo- and Enantioselective Catalytic Diels−Alder Reaction of α,β-Unsaturated Methyl Esters” J. Am. Chem. Soc. 2018, 140, 12671–12676.

(4) T. Gatzenmeier, P. S. J. Kaib, J. B. Lingnau, R. Goddard, B. List “The Catalytic Asymmetric Mukaiyama–Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters” Angew. Chem. Int. Ed. 2018, 57, 2464–2468.

(5) T. Gatzenmeier,^[+] M. van Gemmeren,^[+] Y. Xie, D. Höfler, M. Leutzsch, B. List “Asymmetric Lewis acid organocatalysis of the Diels–Alder reaction by a silylated C–H acid” Science 2016, 351, 949–952.

⁺equal contribution; *corresponding author