4.7 Article

N-Heterocyclic Carbene-Stabilized Palladium Complexes as Organometallic Catalysts for Bioorthogonal Cross-Coupling Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 18, Pages 8652-8658

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo5014228

Keywords

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Funding

  1. National Natural Science Foundation of China [21352002, 21202147]

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A small library of water-soluble N-heterocyclic carbene (NHC)-stabilized palladium complexes was prepared and applied for cross-couplings of biomolecules under mild conditions in water. Pd-NHC complexes bearing hydrophilic groups were demonstrated to be efficient catalysts for the Suzuki-Miyaura coupling of various unnatural amino acids and proteins bearing p-iodophenyl functional groups. We further utilized this catalytic system for the rapid bioorthogonal labeling of proteins on the surfaces of mammalian cells. These results demonstrated that NHC-stabilized metal complexes have potential utility in cellular systems.

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