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

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PdCl2/DMSO-Catalyzed Thiol–Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
Organic Letters ( IF 4.9 ) Pub Date : 2021-04-02 , DOI: 10.1021/acs.orglett.1c00858
Jimin Guo ₁ , Jianjian Zha ₁ , Tao Zhang ₁ , Chang-Hua Ding ₁ , Qitao Tan ₁ , Bin Xu _{1,

2}

Affiliation

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′.

中文翻译：

PdCl ₂ / DMSO催化的巯基-二硫键交换：不对称二硫键的合成

通过使用简单的PdCl ₂ / DMSO催化系统与对称的二硫化物进行硫醇交换，可以有效地制备不对称的二硫化物。给定的方法具有出色的官能团耐受性，广泛的底物范围和操作简便性。该反应对于诸如肽和药物之类的生物活性支架的后期功能化特别有用。还已经制备了含二硫化物的有机染料。这种转化可以扩展到硫醇-二硒化物或硫醇-二碲化物交换，从而提供RS-SeR'或RS-TeR'。

更新日期：2021-04-16

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