Germany: Basic Research Formulation of Fluorinated Molecular Rings Has Great Impact on Development of New Molecules

Chemists led by Prof. Frank Glorius from the University of Münster have developed a new and practical synthetic method for the formation of fluorinated three-dimensional “saturated” molecular ring structures. This development can have great importance for the efficient production of new molecules and, consequently, new drugs, crop protection agents and functional materials.

Münster/Germany — Dyes, pharmaceuticals, and functional materials — all of these products are generally based on innovative molecules made by chemists. For their production several chemical reactions are available to the expert, however, limitations remain.

For example, fluorinated compounds, molecules that contain at least one fluorine atom, are often rather difficult to prepare. This is unfortunate, since they exhibit interesting chemical properties and are of greatest importance for the development of active ingredients. Thus, new ways have to be found to produce these compounds.

Breakthrough Development

Now, chemists from the Westfälische Wilhems-Universität (WWU) made the impossible possible: they have developed a new and practical synthetic method for the formation of such fluorinated three-dimensional “saturated” (meaning only single-bond containing) molecular ring structures. The report of Prof. Dr. Frank Glorius, Mario Wiesenfeldt, Dr. Zackaria Nairoukh and Dr. Wei Li has just been published online in the learned journal “Science“.

“I feel that our results are a breakthrough. It can have great importance for the efficient production of new molecules and, consequently, new drugs, crop protection agents and functional materials” is the assessment of Frank Glorius.

His new synthetic method starts from flat, “aromatic“ (and thus very stable) ring structures built up from carbon and bearing fluorine atoms. These starting materials employed by the Münster scientists are either low priced commercially available compounds or they can be readily made.

Facilitated by a catalyst the chemists succeeded to add hydrogen atoms (“hydrogenation”) selectively to one face of the ring system. Chemists and biochemists define catalysts as enzymes or molecules that can speed up or enable certain reactions. A selective addition allows the control of the properties of the products formed, for example the solubility, the aggregate state or the polarity.

Gallery

A molecule is considered to be “polar”, if charges are separated to result in more negative and more positive molecular fragments. The products formed in this study contain the more negatively charged fluorine atoms on one face and the more positively charged hydrogen atoms on the other face of the ring.

Successful Conversion of Different Materials

Many different fluorinated aromatic starting materials were successfully converted into the desired products by the group of Frank Glorius. “For two reasons the success of our work was rather unexpected” stresses Frank Glorius. “The attached fluorine atoms reduce the reactivity of the already not very reactive aromatic starting materials in the catalytic hydrogenation even further. This is especially true for substrates containing multiple fluorine atoms. Even more pronounced is the sensitivity of the carbon-fluorine bond against hydrogenation, generally leading to the loss of the fluorine atom.”

Many studies of the past had observed this latter problem. Remarkably, the new synthetic method allows fluorine atoms to tolerate the catalytic hydrogenation. “We have identified a catalyst system that is powerful enough to overcome the aromatic stabilization. Yet it is mild enough to preserve the carbon-fluorine bonds.”

As a catalyst the scientists from Münster utilize a combination of the noble metal rhodium and an especially electron-rich carbene-ligand (a special “metal-binding” molecule) that greatly influences the properties of the catalyst.

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