Continuous Flow Synthesis of N-Sulfonyl-1,2,3-triazoles for Tandem Relay Cu/Rh Dual Catalysis

Yong Ju Kwon, Sang Gi Lee, Won Suk Kim

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The continuous flow synthesis of N-sulfonyl-1,2,3-triazoles, which are convenient reactive azavinyl carbene precursors, for tandem relay Cu/Rh dual catalysis has been developed. Most reactions readily proceeded at 75 °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 for the synthesis of various cis-diamino enones from alkynes and sulfonyl azides.

Original languageEnglish
Pages (from-to)1200-1214
Number of pages15
JournalJournal of Organic Chemistry
Volume88
Issue number2
DOIs
StatePublished - 20 Jan 2023

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) (NRF-2022R1F1A1074510, NRF-2022R1I1A1A01071676, NRF-2019M1A2A2072417, NRF-2021R1A6A1A10039823).

Publisher Copyright:
© 2023 American Chemical Society.

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