%0 Journal Article
%T Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly ¦Ã-C(sp3)¨CH Silylation
%J -
%D 2019
%R https://doi.org/10.1021/acscatal.9b00544
%X 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 ¦Ã-C(sp3)¨CH silylation of ¦Á-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 ¦Á-amino acid residues render this protocol a valuable strategy to access ¦Ã-silyl-¦Á-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)¨CH functionalization
%U https://pubs.acs.org/doi/10.1021/acscatal.9b00544