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Article Dans Une Revue European Journal of Organic Chemistry Année : 2020

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

Résumé

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.
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Dates et versions

hal-02910296 , version 1 (01-08-2020)

Identifiants

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Yunxin Yao, Guangkuan Zhao, Abdallah Hamzé, Mouad Alami, Olivier Provot. Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN. European Journal of Organic Chemistry, In press, ⟨10.1002/ejoc.202000979⟩. ⟨hal-02910296⟩
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