The sulfenylation of imidazopyridines with sulfinic acids mediated by DTBP/HCl

A direct sulfenylation reaction of imidazopyridines with sulfinic acid mediated by di- tert -butylperoxide (DTBP) and hydrochloric acid was developed leading to the introduction of C S bonds into the imidazo[1,2- a ]pyridine skeleton. The reaction proceeded under transition-metal-free conditions with good functional group tolerance and moderate to excellent yields. The DTBP/HCl-mediated C-3 sulfenylation of imidazo[1,2- a ]pyridines was developed using readily available and stable sulfinic acids as sulfur source. • t-BuOOBu t /HCl was used to promote the C-3 sulfuration of imidazopyridines. • HCl plays an important role in the formation of Ar-S-O-SO 2 Ar from Ar-SO 2 H. • t-BuOOBu t can efficiently mediate Ar-S-O-SO 2 Ar to generate Ar S radical. • Readily available, odorless and stable RSO 2 H was used as sulfur source. • The method displays broad substrate scope. • Simple operation without metal reagent were used.

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Publication Details

Journal
Results in Chemistry
Published
2025-06-16
DOI
https://doi.org/10.1016/j.rechem.2025.102428
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

The sulfenylation of imidazopyridines with sulfinic acids mediated by DTBP/HCl

Xueyu Fang, Zhaohua Yan, Hua Yao, Yu Wang et al.
Results in Chemistry
Sulfur-Based Synthesis Techniques
article

The sulfenylation of imidazopyridines with sulfinic acids mediated by DTBP/HCl

Xueyu Fang, Zhaohua Yan, Hua Yao, Yu Wang, Chen Tian, Hongkun Huang, Chun Ling
article en

Abstract

A direct sulfenylation reaction of imidazopyridines with sulfinic acid mediated by di- tert -butylperoxide (DTBP) and hydrochloric acid was developed leading to the introduction of C S bonds into the imidazo[1,2- a ]pyridine skeleton. The reaction proceeded under transition-metal-free conditions with good functional group tolerance and moderate to excellent yields. The DTBP/HCl-mediated C-3 sulfenylation of imidazo[1,2- a ]pyridines was developed using readily available and stable sulfinic acids as sulfur source. • t-BuOOBu t /HCl was used to promote the C-3 sulfuration of imidazopyridines. • HCl plays an important role in the formation of Ar-S-O-SO 2 Ar from Ar-SO 2 H. • t-BuOOBu t can efficiently mediate Ar-S-O-SO 2 Ar to generate Ar S radical. • Readily available, odorless and stable RSO 2 H was used as sulfur source. • The method displays broad substrate scope. • Simple operation without metal reagent were used.

Results in ChemistryVol. 16
Nanchang University (CN), Zhejiang Pharmaceutical College (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangxi Province
Clean water and sanitation
Openalex Percentile: Top 90%
Sulfur-Based Synthesis Techniques
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