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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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https://hal-polytechnique.archives-ouvertes.fr/hal-01456154
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Submitted on : Saturday, February 4, 2017 - 10:36:38 AM
Last modification on : Tuesday, September 22, 2020 - 3:59:22 AM

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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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