Electrochemical C-H Activations with 3d and 4d Transition Metal Catalysts

by Leonardo Massignan
Doctoral thesis
Date of Examination:2021-12-02
Date of issue:2021-12-20
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Alexander Breder
Referee:Prof. Dr. Dr. H.c. Lutz Tietze
Referee:Prof. Dr. Manuel Alcarazo
Referee:Dr. Michael John
Referee:Dr. Daniel Janßen-Müller
Persistent Address: http://dx.doi.org/10.53846/goediss-9013

 

 

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Abstract

English

The oxidative metal-catalyzed C–H activation of inert bonds is a powerful tool for the functionalization of complex molecules. This platform allowed the broadening of the organic chemists’ toolbox and improved the resource-economy of synthetic routes, avoiding prefunctionalizations of starting materials. Nevertheless, its applications were constrained by the use of stoichiometric oxidants, which limited the sustainability of this approach. In contrast, the use of electricity as environmental-friendly and versatile oxidant enhanced the sustainability of oxidative metal-catalyzed C–H activation and opened the way to the study of novel reactivities and selectivities. Within this thesis, electrochemical cobalt catalyzed and ruthenium catalyzed annulation reactions were initially studied. The electrochemical approach was then broadened to the C–H oxygenation reactions with ruthenium catalysis enabled by electrogenerated hypervalent iodine species and with rhodium catalysis. In addition, C–H arylation and C–H alkylation reaction by earth-abundant manganese as catalyst and electricity as sustainable oxidant was developed.
Keywords: C–H Activation; Transition Metal Catalysis; Electrochemistry; Ruthenium; Rhodium; Manganese; Cobalt; Hypervalent iodine
 
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