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C–H Activation by Iron(III), Manganese(II) and Rhoda(III)electro Catalysis

by Zhigao Shen
Doctoral thesis
Date of Examination:2020-12-02
Date of issue:2020-12-15
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Konrad Koszinowski
Referee:Prof. Dr. Dr. Lutz Tietze
Referee:Prof. Dr. Manuel Alcarazo
Referee:Dr. Michael John
Referee:Prof. Dr. Johannes C. L. Walker
crossref-logoPersistent Address: http://dx.doi.org/10.53846/goediss-8366

 

 

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Abstract

English

While major progress was realized with noble transition metal catalysts, the employment of cost-effective and earth-abundant 3d metals has gained significant momentum during the last decade. As stoichiometric amounts of oxidants are often needed for the C–H activation, electricity has been identified as aninexpensive, economical, and environmental benign alternative for chemical redox equivalents. Thus, my projects have focused on both the earth-abundant 3d metals and resource-economic electrochemical C–H bond transformations. we achieved an expedient C–H functionalization of electron-rich benzyl and aryl amines by sustainable iron-catalysis with the assistance of a new fully substituted triazole TST directing group enabling C–H methylations, alkylations and arylations. We also developed a direct ortho-alkylation of pyridines by weak assistance of amides.A multifunctional and transformable Omethylamidoxime was designed to guarantee the reactivity and selectivity. The isolation of two C–H-activated rhodacycles offered the proof for sequence of the cascade C–H activation.In the last project, we have developed a bifurcated C–H cyclopropylation and dienylation of indoles by rhodaelectro-catalysis under aqueous conditions, avoiding the use of stoichiometric amounts of chemical oxidants.
Keywords: C H activation; Manganese-catalysis; Iron-catalysis; Cyclopropylation
 

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