Iron-Catalyzed Cross-Coupling of Thioesters and Organomanganese Reagents
Valentin Jacob Geiger1, Guillaume Lefèvre2, Ivana Fleischer1
1Institute of Organic Chemistry, Faculty of Science, Eberhard Karls University Tübingen, Auf der Morgenstelle 18, 72076, Tübingen, Germany.
Abstract:
We report a Fukuyama-type coupling of thioesters with aliphatic organomanganese reagents utilizing a cheap and easily available iron(III) precatalyst. The reactions exhibit a wide tolerance of solvents and functional groups, allowing for the conversion of thioesters derived from natural products and pharmaceutical compounds. A strong steric impact from each reaction component (carboxylic moiety, thiol substituent and manganese reagent) was displayed, which enabled regioselective transformation of dithioesters. Mechanistic investigations showed that the released thiolate does not act as a mere spectator ligand, but rather positively influences the stability of intermediate alkyl(II)ferrates.
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