PdCl2/DMSO-Catalyzed Thiol–Disulfide Exchange: Synthesis of Unsymmetrical Disulfide

Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 8; pp. 3167 - 3172
Main Authors Guo, Jimin, Zha, Jianjian, Zhang, Tao, Ding, Chang-Hua, Tan, Qitao, Xu, Bin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.04.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
GENERATION
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Summary:Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol–diselenide or thiol–ditelluride exchange affording RS–SeR′ or RS–TeR′.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00858