Direct Utilization of Calcium Carbide with Transition Metal‐Free Condition to Synthesize of 1‐Monosubstituted‐1,2,3‐triazoles from Azides

Abstract The utilization of calcium carbide as an acetylide specie was an increasing concern in chemical society. Under transition metal‐ and base free conditions, calcium carbide was successfully proved as the acetylide resource to synthesize 1‐monosubstituted‐1,2,3‐triazoles from nucleophilic addition with azides. In this reaction, aryl azides achieved corresponding 1,2,3‐triazoles in good to excellent yields, and a gram‐scale reaction of phenyl azide with calcium carbide was conducted with an excellent yield. Alkyl azides could also participate in the reaction to prepare corresponding 1,2,3‐triazoles with moderate yield. Calcium acetylide hydroxide Ca(OH)C≡CH might be the critical intermediate. The process provided a green and sustainable prospect to utilize calcium carbide resource.

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Journal
ChemistrySelect
Published
2024-10-01
DOI
https://doi.org/10.1002/slct.202400571
Citations
2
Primary Topic
Click Chemistry and Applications
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article
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0.50
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article

Direct Utilization of Calcium Carbide with Transition Metal‐Free Condition to Synthesize of 1‐Monosubstituted‐1,2,3‐triazoles from Azides

Yuxue Chen, Luyong Wu, Tinghong Tang, Liyi Feng
2 citations
ChemistrySelect
Click Chemistry and Applications
0.50
article

Direct Utilization of Calcium Carbide with Transition Metal‐Free Condition to Synthesize of 1‐Monosubstituted‐1,2,3‐triazoles from Azides

Yuxue Chen, Luyong Wu, Tinghong Tang, Liyi Feng
article en
2 citations

Abstract

Abstract The utilization of calcium carbide as an acetylide specie was an increasing concern in chemical society. Under transition metal‐ and base free conditions, calcium carbide was successfully proved as the acetylide resource to synthesize 1‐monosubstituted‐1,2,3‐triazoles from nucleophilic addition with azides. In this reaction, aryl azides achieved corresponding 1,2,3‐triazoles in good to excellent yields, and a gram‐scale reaction of phenyl azide with calcium carbide was conducted with an excellent yield. Alkyl azides could also participate in the reaction to prepare corresponding 1,2,3‐triazoles with moderate yield. Calcium acetylide hydroxide Ca(OH)C≡CH might be the critical intermediate. The process provided a green and sustainable prospect to utilize calcium carbide resource.

ChemistrySelectVol. 9(38)
Hainan Normal University (CN)
Responsible consumption and production
Openalex Percentile: Top 39%
Click Chemistry and Applications
0.50
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