Photoinduced Carbamoylarylation of Alkynes with <i>N</i>-Aryl Oxamic Acids

1,2-Difunctionalization of alkynes is an attractive synthetic protocol, because it can achieve a high step economy and provide various complex organic molecules. This study demonstrates the visible-light-induced carbamoylarylation of terminal alkynes using <i>N</i>-aryl oxamic acids as bifunctional reagents. The transformation involves the addition of carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)-N bond cleavage to afford the corresponding arylacrylamides in moderate to good yields.

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Publication Details

Journal
Organic Letters
Published
2025-04-03
DOI
https://doi.org/10.1021/acs.orglett.5c00866
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.87

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article

Photoinduced Carbamoylarylation of Alkynes with N-Aryl Oxamic Acids

Akira Shiozuka, Yoichiro Kuninobu, Joji Kajiwara, Kohei Sekine et al.
2 citations
Organic Letters
Sulfur-Based Synthesis Techniques
1.87
article

Photoinduced Carbamoylarylation of Alkynes with N-Aryl Oxamic Acids

Akira Shiozuka, Yoichiro Kuninobu, Joji Kajiwara, Kohei Sekine, Di Wu, Gaofan Yue
article en
2 citations

Abstract

1,2-Difunctionalization of alkynes is an attractive synthetic protocol, because it can achieve a high step economy and provide various complex organic molecules. This study demonstrates the visible-light-induced carbamoylarylation of terminal alkynes using <i>N</i>-aryl oxamic acids as bifunctional reagents. The transformation involves the addition of carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)-N bond cleavage to afford the corresponding arylacrylamides in moderate to good yields.

Organic LettersVol. 27(15)
Kyushu University (JP)
Kyushu University, Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 17%
Sulfur-Based Synthesis Techniques
1.87
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Photoinduced Carbamoylarylation of Alkynes with <i>N</i>-Aryl Oxamic Acids — Akira Shiozuka, Yoichiro Kuninobu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS