ABGESAGT

Stefan M. Huber; Ruhr-University Bochum, Universitätsstraße 150, D-44801 Bochum, Germany

Keywords: Noncovalent Interactions, Organocatalysis, Supramolecular Chemistry

"Noncovalent Organocatalysis with Neutral and Chiral Halogen Bond Donors"

In the last years, a key goal of our research was the development of noncovalent organocatalysis through halogen bonding (XB) [1]. While previously employed polyfluorinated XB donors often suffered from comparably low performance, we now introduce a new type of neutral multidentate halogen bond donors, which markedly exceed the Lewis acidity of the previous polyfluorinated ones [2].

An important current goal of halogen bonding organocatalysis is the realization of enantioselective syntheses. We present the second generation of a bis(iodoimidazolium)-benzene-based catalyst in a highly enantioselective Mukaiyama aldol reaction [3]. Importantly, several control experiments indicate that halogen bonding is decisive for substrate activation and enantioinduction.

In addition, we report on a proof-of-principle case for halogen bonding asymmetric counteranion-directed catalysis (XB-ACDC) in the highly enantioselective Diels-Alder reaction between cyclopentadiene and trans-β-nitrostyrene, the key step in the synthesis of the drug fencamfamine [4].

References:

[1]    Review: D. Jovanovic, M. Poliyodath Mohanan, S. M. Huber, Angew. Chem. Int. Ed. 2024, 63, e202404823.

[2]    C. J. Vonnemann, E. Engelage, J. S. Ward, K. Rissanen, S. Keller,. S. M. Huber, Angew. Chem. Int. Ed. 2025, 64, e202424072.

[3]    J. Wolf, M. Poliyodath Mohanan, R. Sutar, E. Engelage, S. M. Huber, Angew. Chem. Int. Ed. 2025, e202506476.

[4]    D. L. Reinhard, A. Iniutina, S. Reese, T. Shaw, C. Merten, B. List, S. M. Huber, J. Am. Chem. Soc. 2025, 147, 8107-8112.

Biography:

Stefan M. Huber received his Ph.D. in 2007 from the Friedrich-Alexander-University in Erlangen (Germany), working on indigoid ethene derivatives with Robert Weiss. From 2008-2009 he was a postdoctoral fellow at the University of Minnesota in Minneapolis (USA) with Christopher J. Cramer and at the University of Geneva (SUI) with Laura Gagliardi in the field of computational chemistry. After a short postdoctoral stint in Erlangen, he started his independent career at Technische Universität München (Germany) under the mentorship of Thorsten Bach. In 2014, he moved to Ruhr-University Bochum (Germany) as Associate Professor and was promoted to Full Professor in 2022.

He has received several prizes, including scholarships by the German Academic Scholarship Foundation (Studienstiftung des Deutschen Volkes), the Robert Sauer prize by the Bavarian Academy of Sciences, and an ERC Starting Grant. His research interests focus on the use of “unconventional” noncovalent interactions like halogen and chalcogen bonding in solution, particularly in organocatalysis.

Representative Publications:

1.         S. M. Walter, F. Kniep, E. Herdtweck, S. M. Huber, Halogen-Bond-Induced Activation of a Carbon-Heteroatom Bond, Angew. Chem. Int. Ed. 2011, 50, 7187.

2.         S. H. Jungbauer, D. Bulfield, F. Kniep, C. W. Lehmann, E. Herdtweck, S. M. Huber, Toward Molecular Recognition: Three-Point Halogen Bonding in the Solid State and in Solution, J. Am. Chem. Soc. 2014, 136, 16740.

3.         P. Wonner, A. Dreger, L. Vogel, E. Engelage, S. M. Huber, Chalcogen Bonding Catalysis of a Nitro-Michael Reaction, Angew. Chem. Int. Ed. 2019, 58, 16923.

4.         F. Heinen, D. L. Reinhard, E. Engelage, S. M. Huber, A Bidentate Iodine(III)‐Based Halogen‐Bond Donor as a Powerful Organocatalyst, Angew. Chem. Int. Ed. 2021, 60, 5069.