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Germany: Basic Research

Formulation of Fluorinated Molecular Rings Has Great Impact on Development of New Molecules

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First author Mario Wiesenfeldt summarizes: “The new method provides surprisingly simple access to a fascinating structural motif: cyclic, saturated and selectively fluorinated on one face. Many of the products are characterized by a high level of polarity.”

Large Amounts Easily Prepared in One Step

Some background information: The compound “all-cis-1,2,3,4,5,6-hexafluorocyclohexane“, in which the saturated six-membered carbon-cycle contains the maximum number of 6 fluorine atoms on the same face of the ring, represents one of the most polar organic molecules known to date. Only in 2015 this remarkable compound was first prepared and reported by Prof. David O’Hagan from the University of St. Andrews in Scotland. However, his team required a twelve-step synthetic sequence for its formation. The new method allows the formation of this and many related compounds in a convenient single step, thus allowing the formation of larger amounts.

Asymmetric hydrogenation of arenes as a remaining challenge

“Hydrogenation is an attractive and often very clean method of synthesis“ stresses Frank Glorius. “An especially prominent example is the formation of ammonia through the Haber-Bosch process, the hydrogenation of nitrogen, consuming more than 1 % of the world's annual energy supply.

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It is of fundamental importance for the nutrition of mankind, since it serves as a basis for the production of nitrogen fertilizer, among others.“ In addition the importance is also reflected by the three Nobel prizes given for this topic (Fritz Haber 1918, Carl Bosch 1931, Gerhard Ertl 2007).

Also important is the hydrogenation of organic compounds, last decorated with a Nobel price for the asymmetric hydrogenation of aromatic compounds in 2001 (William S. Knowles und Ryoji Noyori). Chemoselective and asymmetric hydrogenation reactions of aromatic compounds remain to be challenging.

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