Nickel Catalyzed Cross Couplings of Amino Acids and Peptide Derivatives via C-N Bond Activation

Primary alkyl amines are well appreciated as building blocks for the synthesis of nitrogen‐containing molecules. However, their use as alkylating agents via cleavage of the carbon–nitrogen (C–N) bond is largely undeveloped. Recognizing this opportunity to expand the utility of alkyl amines in synthesis, the M. Watson group is developing strategies to convert primary alkyl amines into alkyl arenes via nickel‐ catalyzed cross‐couplings of Katrizky pyridinium salt intermediates. We are now developing this chemistry to enable cross‐couplings of alpha‐amino acids and peptides via cleavage of the alpha‐C–N bond. Pyridinium salts were formed from the N‐termini of a number of α‐amino acids and a tripeptide, prepared via solid phase peptide synthesis. Once formed, the pyridinium salts were allowed to undergo nickel‐catalyzed cross‐coupling. Our preliminary scope, as well as future work, will be presented. Support or Funding Information The National Institutes of Health (R01 GM111820) University of Delaware David A. Plastino Fellowship This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .