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Iron-Catalyzed Aryl-Aryl Cross-Coupling Reaction: Homo-versus Hetero-Coupling Reactions

Abstract : An in-depth mechanistic study was undertaken to explain the competition between the homo-and heterocoupling reactions in the case of iron-catalyzed aryl-aryl cross-couplings in the presence of C$_6$F$_5$Cl as an organic sacrificial oxidant. The formation of the homocoupling product is explained by a crucial iron-to-magnesium transmetallation of a C$_6$F$_{5─}$ anion arising from the bielectronic reduction of C6F5Cl. This mechanism is discussed and supported by experimental results, including $^1$H paramagnetic NMR and $^{57}$Fe-Mössbauer spectroscopies. These results enlighten the mechanistic features of iron-catalyzed Grignard oxidative homocoupling, and can provide guidance in the choice of suitable sacrificial oxidants for such systems.
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Submitted on : Wednesday, October 30, 2019 - 2:35:57 PM
Last modification on : Monday, July 4, 2022 - 8:50:08 AM


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  • HAL Id : cea-02339520, version 1


E. Zhou, Lidie Rousseau, M. Ahr, M. Clemancey, J.-M Latour, et al.. Iron-Catalyzed Aryl-Aryl Cross-Coupling Reaction: Homo-versus Hetero-Coupling Reactions. International Symposium on Synthesis and Catalysis (ISYSYCAT 2019), Sep 2019, Evora, Portugal. ⟨cea-02339520⟩



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