Late-Stage Peptide Functionalization by Transition Metal-free and Palladium-Catalyzed C–H Arylations

by Michaela Bauer
Doctoral thesis
Date of Examination:2022-03-08
Date of issue:2022-03-31
Advisor:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Lutz Ackermann
Referee:Prof. Dr. Dietmar Stalke
Referee:Prof. Dr. Manuel Alcarazo
Referee:Prof. Dr. Sven Schneider
Referee:Prof. Dr. Johannes C. L. Walker
Referee:Dr. Michael John
Persistent Address: http://dx.doi.org/10.53846/goediss-9157

 

 

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Abstract

English

The focus of this thesis was set on the late-stage modification of peptides through transition metal-free and palladium-catalyzed C–H arylations. At first, the scope of the transition metal-free C2-arylation of the indolylacetamid moiety incorporated into peptides as a tag at the N-terminus with diaryliodonium tosylates was explored. Thereafter, the direct C–H arylation of tryptophan-containing peptides with diaryliodonium tosylates under palladium catalysis was accomplished. Finally, the palladium-catalyzed arylation of primary and secondary C(sp3)–H bonds of amino acids and peptides with aryl iodides using triazole assistance was investigated. The developed procedures had a broad scope with excellent functional group tolerance enabling peptide ligation and labeling with fluorophores.
Keywords: C-H Activation; metal-free; Palladium; tryptophan; late-stage functionalization; triazole directing group; indole
 
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