Panda, Satya Prakash and Prasad, M. Siva and Meher, Prahallad and Reiser, Oliver and Murarka, Sandip (2025) Iron photocatalysis towards site-selective C(sp3)-H alkylation of glycines and peptides. CHEMICAL SCIENCE, 16 (46). pp. 22084-22090. ISSN 2041-6520, 2041-6539
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Utilizing iron-mediated ligand-to-metal charge transfer (LMCT) photocatalysis provides a sustainable platform for generating carbon-centered radicals. This study presents the use of abundant and inexpensive iron as a photocatalyst to easily activate aliphatic carboxylic acids, producing Csp3 radicals for site-selective C(sp3)-H alkylation of glycines and peptides. The method exhibits broad applicability, cost-effectiveness, and excellent tolerance to various functional groups. It is a flexible and efficient approach applicable to the synthesis of various unnatural alpha-amino acids and enables peptide drug bioconjugation. In addition to secondary and tertiary radicals, the iron-LMCT system enables access to primary radicals and the highly unstable methyl radical, derived from acetic acid, facilitating the production of methylated glycine derivatives. Preliminary mechanistic studies suggest a reaction pathway involving an Fe(iii)-Fe(ii)-Fe(iii) redox cycle and radical-radical cross-coupling.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOREDOX CATALYSIS |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 May 2026 05:41 |
| Last Modified: | 06 May 2026 05:41 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66530 |
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