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Ligand-Enabled Copper-Catalyzed <i>N</i>-Alkynylation of Sulfonamide with Alkynyl Benziodoxolone: Synthesis of Amino Acid-Derived Ynamide
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- Ryogo Takai
- Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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- Daisuke Shimbo
- Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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- Norihiro Tada
- Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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- Akichika Itoh
- Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
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Description
Ynamides are versatile building blocks in organic synthesis. However, the synthesis of amino acid-derived ynamides is difficult but in high demand. Herein, we disclose the copper-catalyzed Csp-N coupling of sulfonamide, including amino acid and peptide derivatives, to give ynamides by using alkynyl benziodoxolones with broad functional group tolerance under mild reaction conditions. The electron-rich bipyridine as a ligand and ethanol as solvent were used for the success of this reaction. The usefulness of the obtained amino acid-derived ynamide as building block was showcased by further derivatization to unique amino acid derivatives. A control experiment to elucidate the mechanistic insight was also described.
Journal
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 86 (6), 4699-4713, 2021-03-10
American Chemical Society (ACS)
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Keywords
- Amino Acid-Derived Ynamide Ynamides
- control experiment
- Chemical Sciences not elsewhere classified
- synthesis
- Physiology
- Information Systems not elsewhere classified
- group tolerance
- electron-rich bipyridine
- Biochemistry
- reaction conditions
- building blocks
- peptide derivatives
- acid-derived ynamide
- Alkynyl Benziodoxolone
- acid derivatives
- Molecular Biology
- building block
- copper-catalyzed Csp-N
- alkynyl benziodoxolones
- Infectious Diseases
- acid-derived ynamides
- Medicine
- Neuroscience
- Biotechnology
- Biological Sciences not elsewhere classified
Details 詳細情報について
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- CRID
- 1360290617664795520
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- ISSN
- 15206904
- 00223263
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- Article Type
- journal article
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- Data Source
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- Crossref
- KAKEN
- OpenAIRE
