TiCl4-Mediated Preparation of Thiophthalide Derivatives via Formal Thio-Passerini Reactions

Abstract : By the formal extension of the Passerini reaction to thiocarbonyl derivatives, the straightforward preparation of thiophthalides is disclosed. This method involves the intermediate formation of a sulfanyl-phthalide and a titanium tetrachloride mediated isocyanide insertion reaction. When tent-butyl thiol is used, thanks to the deprotection of the tert-butyl group, a thiophthalide resulting from a 1,5-Mumm rearrangement is isolated. Owing to the multifaceted activity of TiCl4, all steps may conveniently be performed in one pot, starting directly from 2-formylbenzoic acids, tert-butyl thiol, and various isocyanides.
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Article dans une revue
Organic Letters, American Chemical Society, 2016, 18 (16), pp.4060-4063. 〈10.1021/acs.orglett.6b01937〉
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Soumis le : samedi 4 février 2017 - 10:36:38
Dernière modification le : jeudi 10 mai 2018 - 02:07:40

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Sudipta Ponra,, Aude Nyadanu,, Laurent El Kaim, Laurence Grimaud, Maxime R. Vitale. TiCl4-Mediated Preparation of Thiophthalide Derivatives via Formal Thio-Passerini Reactions. Organic Letters, American Chemical Society, 2016, 18 (16), pp.4060-4063. 〈10.1021/acs.orglett.6b01937〉. 〈hal-01456154〉

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