Development of building blocks for the synthesis of N-heterocyclic carbene ligands.
[reaction: see text] The synthesis of a series of NHC building blocks that can then be incorporated into more complicated structures by palladium catalysis is reported. This approach is used for the synthesis of three amino acids containing NHC side chains. The ability to use the amino acids in solid-phase peptide synthesis to make NHC-containing peptides is also demonstrated. Additionally, the NHC side chain can be deprotected and coordinated to a catalytically active transition metal. Finally, it is illustrated that the building blocks participate in Suzuki coupling to provide access to substituted NHC ligands.
Xu
Guopin
G
Chemical Biology Program, Department of Pharmacology and Toxicology, University of Texas Medical Branch, Galveston, Texas 77555-06309, USA.
Gilbertson
Scott R
SR
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
D000596:Amino Acids; D006571:Heterocyclic Compounds; D006838:Hydrocarbons; D008024:Ligands; C030011:carbene; D010165:Palladium; D008697:Methane