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Organocatalytic Activation of Inert Hydrosilane for Peptide Bond Formation

Wataru Muramatsu* and Hisashi Yamamoto*

*Peptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan, Email:,

W. Muramatsu, H. Yamamoto, Org. Lett., 2022, 24, 7194-7199.

DOI: 10.1021/acs.orglett.2c02947


HSi[OCH(CF3)2]3 catalyzes a reliable protocol for peptide bond formation in high yield that is generally applicable to natural and unnatural α-amino acids, β-amino acids, and peptides bearing various functional groups. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.

see article for more examples

proposed mechanism

Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N- and C-Termini of Dipeptide

T. Hattori, H. Yamamoto, J. Am. Chem. Soc., 2022, 144, 1758-1765.

Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents

W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2021, 143, 6792-6797.

Tantalum-Catalyzed Amidation of Amino Acid Homologues

W. Muramatsu, H. Yamamoto, J. Am. Chem. Soc., 2019, 141, 18926-18931.

Key Words


ID: J54-Y2022