Synthesis of Proline-Based N-Heterocyclic Carbene Building Blocks and Their Applications



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The synthesis of novel proline-based N-heterocyclic carbene ligands has been accomplished. These types of imidazolium salts can be used as building blocks for the synthesis of more sophisticated N-heterocyclic carbene precursors. The proline amino acids are shown to be compatible with peptide synthetic methods by incorporation into tripeptides. The approaches to a variety of bidentate ligand precursors was reported. A number of the ligands synthesized were bound to rhodium through transmetallation of a silver-NHC complex.



Synthesis, N-heterocyclic carbene, Amino acid, Peptide, Ligands, Catalysis


Portions of this document appear in: Zhao, Yang, and Scott R. Gilbertson. "Synthesis of Proline-Based N-Heterocyclic Carbene Ligands." Organic letters 16, no. 4 (2014): 1033-1035. The material from this article is from the accepted manuscript of a published work that appeared in final form in Organic Letters. The version of record for that article is available at the following DOI: 10.1021/ol403465d.