Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes,The Journal of Organic Chemistry

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Pd/PTABS: Low-Temperature Thioetherification of Chloro(hetero)arenes
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-06-10 00:00:00 , DOI: 10.1021/acs.joc.9b00840
Siva Sankar Murthy Bandaru ₁ , Shatrughn Bhilare ₂ , Jesvita Cardozo ₂ , Nicolas Chrysochos ₁ , Carola Schulzke ₁ , Yogesh S. Sanghvi ₃ , Krishna Chaitanya Gunturu ₄ , Anant R. Kapdi _{2,

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Affiliation

The thioetherification of heteroaryl chlorides is an essential synthetic methodology that provides access to bioactive drugs and agrochemicals. Due to their (actual or potential) industrial importance, the development of efficient and low-temperature protocols for accessing these compounds is a requirement for economic and ecologic reasons. A particular highly effective catalytic protocol using the Pd/PTABS system at only 50 °C was developed accordingly. The coupling between chloroheteroarenes and a variety of less reactive arylthiols and alkylthiols was carried out with a high efficiency. Heteroarenes of commercial relevance such as purines and pyrimidines were also found to be useful substrates for the reported transformation. The commercial drug Imuran (azathioprine) was synthesized as an example, and its preparation could be optimized. DFT studies were performed to understand the electronic effects of the tested ligands on the catalytic reaction.

中文翻译：

Pd / PTABS：氯（杂）芳烃的低温硫醚化

杂芳基氯化物的硫醚化是必不可少的合成方法，可用于获得生物活性药物和农药。由于它们的（实际或潜在的）工业重要性，出于经济和生态方面的原因，需要开发一种有效的低温协议来获取这些化合物。因此，开发了一种仅在50°C下使用Pd / PTABS系统的高效催化方案。高效率地进行了氯杂芳烃与各种反应性较低的芳基硫醇和烷基硫醇之间的偶联。还发现具有商业意义的杂芳烃，例如嘌呤和嘧啶，是报道的转化的有用底物。以合成的商品药物Imuran（硫唑嘌呤）为例，可以优化其制备方法。

更新日期：2019-06-10

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