Visible-Light-Induced Carbamoylation for Synthesis of Dibenzo[ <i>b,f</i> ][1,4]oxazepine Carbonyl Amino Acid/Peptide Derivatives

Introducing amino acids/peptides onto the heterocycle via photocatalytic methods remains a significant challenge. A novel visible-light-driven carbamoylation approach was first developed, facilitating the efficient synthesis of dibenzo[<i>b,f</i>][1,4]oxazepine carbonyl amino acid/peptide derivatives (>40 examples, up to 98% yield) from DHP-tagged amino acids/peptides. This strategy offers mild reaction conditions, easy scale-up, broad substrate compatibility, environmental friendliness, simple operation, and high tolerance to diverse functional groups. In addition, it enables late-stage functionalization of amine-containing drugs/natural products/proteins.

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Publication Details

Journal
Organic Letters
Published
2026-02-18
DOI
https://doi.org/10.1021/acs.orglett.6c00032
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-Induced Carbamoylation for Synthesis of Dibenzo[ b,f ][1,4]oxazepine Carbonyl Amino Acid/Peptide Derivatives

Yanli Yin, Jianan Chen, Fan-Lin Zeng, Yuxin Luo et al.
Organic Letters
Radical Photochemical Reactions
article

Visible-Light-Induced Carbamoylation for Synthesis of Dibenzo[ b,f ][1,4]oxazepine Carbonyl Amino Acid/Peptide Derivatives

Yanli Yin, Jianan Chen, Fan-Lin Zeng, Yuxin Luo, Teck-Peng Loh
article en

Abstract

Introducing amino acids/peptides onto the heterocycle via photocatalytic methods remains a significant challenge. A novel visible-light-driven carbamoylation approach was first developed, facilitating the efficient synthesis of dibenzo[<i>b,f</i>][1,4]oxazepine carbonyl amino acid/peptide derivatives (>40 examples, up to 98% yield) from DHP-tagged amino acids/peptides. This strategy offers mild reaction conditions, easy scale-up, broad substrate compatibility, environmental friendliness, simple operation, and high tolerance to diverse functional groups. In addition, it enables late-stage functionalization of amine-containing drugs/natural products/proteins.

Organic LettersVol. 28(9)
Nanyang Technological University (SG), Department of Biotechnology (IN), Henan University of Technology (CN), Henan Normal University (CN)
Life in Land
Openalex Percentile: Top 48%
Radical Photochemical Reactions
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