Improved Route To OCF3 Building Blocks | January 3, 2011 Issue - Vol. 89 Issue 1 | Chemical & Engineering News
Volume 89 Issue 1 | pp. 23-24 | Concentrates
Issue Date: January 3, 2011

Improved Route To OCF3 Building Blocks

Versatile strategy improves the synthesis of aliphatic organic molecules containing trifluoromethoxy groups
Department: Science & Technology
Keywords: trifluoromethyl, chemical intermediate, medicinal chemistry, agricultural chemical
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Using KOCF3, chemists prepared trifluoromethoxy-substitutedaliphatic compounds that can be further modified, such as this alkene thatwas converted to an epoxide.
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Using KOCF3, chemists prepared trifluoromethoxy-substitutedaliphatic compounds that can be further modified, such as this alkene thatwas converted to an epoxide.

A new synthetic strategy for introducing the trifluoromethoxy group into aliphatic organic molecules is a promising way to make pharmaceutical and agricultural chemicals, according to Karsten Koppe of Heinrich Heine University, in Düsseldorf, Germany. The OCF3 group is strongly electron withdrawing and offers advantages such as increased lipophilicity over popular F or CF3 substituents that are commonly used to improve drug efficacy. Although an industrial process using chlorine-fluorine exchange to prepare OCF3-containing aromatic compounds exists, there are few examples of procedures to make aliphatic compounds bearing OCF3 groups, and they are limited in scope, Koppe said. Koppe and coworkers, in collaboration with Nikolai V. Ignat’ev of Merck KGaA, in Darmstadt, Germany, devised a method that uses OCF3 salts to introduce OCF3 to aliphatic compounds bearing different functional groups. For example, the researchers prepared KOCF3 by adding CF3SO2OCF3 to KF in N,N-dimethylacetamide solvent. Adding organic halides or mesylates to KOCF3 results in the trifluoromethoxy compounds, which can be derivatized to create epoxides, diols, aminoalcohols, and other intermediates, Koppe said, “giving us a whole factory of OCF3 building blocks.”

 
Chemical & Engineering News
ISSN 0009-2347
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