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Continuous Flow Synthesis of N-Sulfonyl-1,2,3-triazoles for Tandem Relay Cu/Rh Dual Catalysis
- Title
- Continuous Flow Synthesis of N-Sulfonyl-1,2,3-triazoles for Tandem Relay Cu/Rh Dual Catalysis
- Authors
- Kwon, Yong-Ju; Lee, Sang-gi; Kim, Won-Suk
- Ewha Authors
- 이상기; 김원석; 권용주
- SCOPUS Author ID
- 이상기; 김원석; 권용주
- Issue Date
- 2023
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- ISSN
- 0022-3263
1520-6904
- Citation
- JOURNAL OF ORGANIC CHEMISTRY vol. 88, no. 2, pp. 1200 - 1214
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- The continuous flow synthesis of N-sulfonyl-1,2,3triazoles, which are convenient reactive azavinyl carbene precursors, for tandem relay Cu/Rh dual catalysis has been developed. Most reactions readily proceeded at 75 degrees C in a short residence time of 13.09 min in the presence of 2.5 mol % of CuTC. The scope of the reactions was explored by synthesizing diversely functionalized N-sulfonyl and sulfamoyl triazoles in yields ranging from 92 to 98%. To demonstrate the scalability of the process, the reaction was conducted on a 5.4 mmol scale with residence and collection times of 13.09 and 60 min, respectively. Furthermore, a series of controlled experiments were performed to investigate the compatibility of Cu and Rh in a batch or a continuous flow system. Finally, the first integrated flow system using the azavinyl carbene intermediate under the tandem relay Cu/Rh dual catalysis was developed alkynes and sulfonyl azides.
- DOI
- 10.1021/acs.joc.2c028081200J
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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