Chalcogen-Bonding-Enabled, Light-Driven Decarboxylative Oxygenation of Amino Acid Derivatives and Short Peptides using O2.

• Tác giả: Feng Li, Yuzheng Li, Shenpeng Tan, Taiqiang Ye
• Ngôn ngữ: eng
• Ký hiệu phân loại: 940.53185092 1918
• Thông tin xuất bản: Germany : Angewandte Chemie (International ed. in English) , 2025
• Bộ sưu tập: NCBI
• ID: 727677

Tóm tắt

Here we report a photocatalytic method for the decarboxylative oxygenation of amino acid derivatives and short peptides using dioxygen as a green oxidant. A reverse catalytic strategy utilizing Lewis basic diphenyl diselenide as a Lewis acid catalyst to activate carboxylic acid via chalcogen bonding interaction is the key to this work. This synthetic method is tolerant of functionalities present in both natural and non-proteinogenic amino acids, enabling the efficient synthesis of C-terminal amides or imides. Mechanistic studies suggest there is a dual noncovalent interaction between diphenyl diselenide and carboxylic acid, which allows radical decarboxylation through photoinduced intermolecular electron transfer. This new activation mode of carboxylic acids will add a new dimension to classical decarboxylative reactions.