Metal‐, Oxidant‐, and Additive‐Free Sulfenylation of Imidazo[1,2‐a]pyridines Using Sulfenamides and an I2 Catalyst

A novel sulfenylation reagent (sulfenamide) was applied to establish a simple and efficient process to convert C−H bond in imidazo[1,2‐a]pyridine to C−S bond. This process only requires sulfenamides as the sulfenylation reagent and I2 as an inexpensive and readily available catalyst, without using m...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2023-08, Vol.12 (8), p.n/a
Main Authors: Qiao, Huijie, Zhao, Kun, Zhu, Xilin, Xu, Xiaoxu, Wang, Chunyang, Zhong, Lulu, Wang, Shixing, Yang, Liting, Yang, Dehong, Liu, Guoqun, Lin, Chunlei, Jiao, Mingli
Format: Article
Language:English
Subjects:
additive-free
C3−H sulfenylation
imidazo[1,2-a]pyridines
iodine catalysis
metal-free
oxidant-free
sulfenamides
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Summary:A novel sulfenylation reagent (sulfenamide) was applied to establish a simple and efficient process to convert C−H bond in imidazo[1,2‐a]pyridine to C−S bond. This process only requires sulfenamides as the sulfenylation reagent and I2 as an inexpensive and readily available catalyst, without using metal catalysts, oxidants, additives, or even light radiation. The proposed reaction features excellent reactivity, substrate compatibility, and regioselectivity. Sulfenamides were used as the novel sulfenylation agent to selectively construct C−S bond at the C3 position of imidazo[1,2‐a]pyridines, using I2 as the catalyst under metal‐free, additive‐free and light‐irradiation‐free conditions. Different imidazo[1,2‐a]pyridine derivatives and sulfenamides could react successfully to generate the target products at medium‐to‐high yields. Mechanistic studies suggested that the reaction involves ion conversion rather than radical conversion.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300292