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Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly γ‑C(sp3)–H Silylation

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journal contribution
posted on 2019-03-12, 00:00 authored by Bei-Bei Zhan, Jun Fan, Liang Jin, Bing-Feng Shi
Silicon-containing peptides hold great promise for maintaining or enhancing biological activity, while simultaneously improving the proteolytic stability. Herein, we report the Pd­(II)-catalyzed γ-C­(sp3)–H silylation of α-amino acids and peptides. Quinone-type ligands play a pivotal role in this reaction, and hexamethyldisilane was used as silylation reagent. The facile removal of a picolinamide auxiliary and the compatibility with a wide range of oligopeptides bearing various α-amino acid residues render this protocol a valuable strategy to access γ-silyl-α-amino acids and peptides. This reaction enriches the chemical toolbox for the site-specific peptide modification and showcases the vast potential of postsynthetic diversification of peptides via late-stage C­(sp3)–H functionalization.