Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN,European Journal of Organic Chemistry

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Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-08-12 , DOI: 10.1002/ejoc.202000979
Yunxin Yao ₁ , Guangkuan Zhao ₁ , Abdallah Hamze ₁ , Mouad Alami ₁ , Olivier Provot ₁

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A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also showed that nitrogenated-substrates as hydrazones, N-tosylhydrazones and ketimes reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

中文翻译：

在 CH3CN 中通过 TMSCl/NaI 缔合对二硫缩醛进行温和脱保护

在乙腈中使用 TMSCl 和 NaI 组合的温和工艺用于从各种二噻烷和二硫戊环衍生物中再生羰基化合物。这种易于操作且价格低廉的方案还可以有效地将含氧和混合缩醛作为 1,3-二氧六环、1,3-二氧戊环和 1,3-氧杂环己烷进行定量脱保护。作为该方法的可能扩展，还表明作为腙、N-甲苯磺酰腙和酮时的氮化底物在这些条件下反应良好，以高产率得到预期的酮。本文提出的方法是现有方法的一个很好的替代方案，因为它不使用金属、氧化剂、还原剂、酸性或碱性介质，并且以高产率获得酮产物。

更新日期：2020-08-12

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