TfOH-Mediated Synthesis of Unsymmetrical Disulfides from Diethyl 2,2’-Disulfanediylbis(4-methyl-6-phenylpyrimidine-5-carboxylate)

A novel approach for the S-S bond exchange reaction of two symmetrical disulfides, promoted by TfOH under metal-free conditions at room temperature, has been developed. This protocol facilitates the efficient and effortless synthesis of a series of important unsymmetrical disulfides with yields of up to 93% and excellent functional group compatibility. The advantages of this strategy include straightforward operation, broad substrate scope, good functional group tolerance, high chemoselectivity, and the ability to operate under ambient conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-26
DOI
https://doi.org/10.1021/acs.joc.5c01287
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

TfOH-Mediated Synthesis of Unsymmetrical Disulfides from Diethyl 2,2’-Disulfanediylbis(4-methyl-6-phenylpyrimidine-5-carboxylate)

Dong‐Yu Miao, Xi‐Cun Wang, Jiao Li, Guo-Qing Sun et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

TfOH-Mediated Synthesis of Unsymmetrical Disulfides from Diethyl 2,2’-Disulfanediylbis(4-methyl-6-phenylpyrimidine-5-carboxylate)

Dong‐Yu Miao, Xi‐Cun Wang, Jiao Li, Guo-Qing Sun, Ming Li, Dong‐Ping Chen, Zheng‐Jun Quan, Zhao‐Zhen Zhou
article en

Abstract

A novel approach for the S-S bond exchange reaction of two symmetrical disulfides, promoted by TfOH under metal-free conditions at room temperature, has been developed. This protocol facilitates the efficient and effortless synthesis of a series of important unsymmetrical disulfides with yields of up to 93% and excellent functional group compatibility. The advantages of this strategy include straightforward operation, broad substrate scope, good functional group tolerance, high chemoselectivity, and the ability to operate under ambient conditions.

The Journal of Organic ChemistryVol. 90(35)
Northwest Normal University (CN)
Northwest Normal University, National Natural Science Foundation of China, Natural Science Foundation of Gansu Province
Openalex Percentile: Top 83%
Sulfur-Based Synthesis Techniques
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