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Synthesis 2022; 54(02): 490-498
DOI: 10.1055/a-1592-6394
DOI: 10.1055/a-1592-6394
paper
Tetrabutylammonium Iodide Mediated Sulfenylation of Polysubstituted 1H-Pyrazol-5-amines with Arylsulfonyl Hydrazides
We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (No. 21563025).
Abstract
A TBAI-mediated sulfenylation of N,3-diaryl-1-arylsulfonyl-1H-pyrazol-5-amines with arylsulfonyl hydrazides has been established, and an expanded inventory of N,5-diaryl-4-(arylthio)-1H-pyrazol-3-amines was constructed through C–S bond formation and N–S bond breaking. Mechanistic investigations suggest thiosulfonate as a key intermediate in the sulfenylation, and the detosylation is promoted by the generated arylsulfinic acid. The method is characterized by simple operating conditions, broad substrate range as well as gram-scale reaction.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1592-6394.
- Supporting Information
Publication History
Received: 28 July 2021
Accepted after revision: 19 August 2021
Accepted Manuscript online:
19 August 2021
Article published online:
12 October 2021
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