Resource-Economical C–H Activation for Late-Stage Functionalization

by Nikolaos Kaplaneris
Doctoral thesis
Date of Examination:2021-06-30
Date of issue:2021-07-07
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Konrad Koszinowski
Referee:Prof. Dr. Dr. h.c. Lutz Tietze
Referee:Prof. Dr. Ricardo Mata
Referee:Dr. Michael John
Referee:Dr. Daniel Janßen-Müller
Persistent Address: http://dx.doi.org/10.53846/goediss-8712

 

 

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Abstract

English

Organic synthesis has traditionally relied on step-, time- and resource-intensive strategies, namely the functional group interconversion and, more recently, on cross-coupling reactions. These approaches have enabled the synthetic community to synthesize every imaginable molecule, given the necessary time and resources. Thus, the next major challenge in the field of organic synthesis is the efficiency, scalability, and sustainability. In this context, transition metal-catalyzed C–H activation has emerged as a powerful tool, as the time- and resource-consuming prefunctionalizations of starting materials are minimized, since inert and omnipresent C–H bonds are utilized as latent functional groups. In this thesis, the primary focus was the development of novel strategies for increasing the molecular complexity of simple precursors via an one-pot difunctionalization approach and the late-stage diversification of peptides. Moreover, in order to address the need for more environmentally-benign C–H transformations we focused on the use of inexpensive Earth-abundant 3d transition metals, namely manganese and cobalt.
Keywords: late-stage functionalization; manganese catalysis; peptides; C–H activation
 
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