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Structural Motif Biaryls

The widespread structural motif of biaryls can be found in natural and active substances, materials science, and chemical catalysts, among other areas.

Our institute's research activities focus in particular on axially chiral biaryls. These have sterically demanding residues in the vicinity of the C-C axis, which prevents free rotation around it. This leads to the formation of configuratively stable enantiomers.

We focus on two areas: firstly, the synthetic access to building blocks and, secondly, the development of innovative synthesis routes to the biaryl motif.

Building blocks are molecules from which divergent synthesis routes lead to a wide variety of relevant molecules. For example, a common precursor for the natural products viriditoxin, isokotanin A, and gonytolid A has already been identified and made accessible via robust and scalable synthetic routes. However, the possible applications are not limited to the synthesis of natural products, as such common platforms also enable access to chiral (organo)catalysts, for example.

Research into novel approaches to axial chiral compounds is one of the main focuses of the institute's basic research. The insights gained in this process expand the chemical space that can be addressed by all synthetic chemists. In addition to classical methods of synthetic chemistry, computer-aided chemistry methods are also used in this research to explain the observed phenomena and make them usable for further development.

Recent Publications

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| BOC

Asymmetric synthesis of C-N-axially chiral carbazoles

We are pleased to announce the publication of our latest research results in the journal Organic & Biomolecular Chemistry under the title ‘Asymmetric Synthesis of C-N Axially Chiral Carbazoles via Axial-to-Axial Chirality Transfer’.

In it, Sebastian Myllek describes the targeted synthesis of C-N-axially chiral carbazole derivatives. These are formed via intramolecular Buchwald-Hartwig amination of C-C-axially chiral biarylenes through an axial-axial chirality transfer.

In parallel, the…
| BOC

Cyclic diaryliodonium salts for the synthesis of 8,8''-biflavones

In his latest publication in Organic Letters, Moritz Klischan et al. used a cyclic diaryliodonium salt to synthesize 8,8''-biflavones for the first time.

By enantioselective ring opening of the diaryliodonium salt 2, both enantiomers of the 2,2-iodobiaryl 3 were obtained, from which the 1,3,5-substituted biaryl 4 was first synthesized. Based on this, both enantiomers of the bisphenol 5 with high ee were synthesized, from which a library of 8,8''-biflavones 6 with activity against HeLa cells was…
| BOC

8,8′-Biflavone Synthesis

The work of Moritz Klischan et al. dealt with the synthesis of a library of non-natural 8,8'-biflavones. To overcome the problems of chemoselectivity, he synthesized the key intermediate acetophenone dimer via a one-step oxidative coupling process. Finally, the synthesis could be performed on an 8 g scale without column chromatographic isolation, synthesizing 14 flavones and 13 biflavones according to the established protocol.

Additionally, antiproliferative activity of the compounds against T.…

The following people work in this area: