title: 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 tert-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.
authors.affiliation: PSL Research University , Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, Paris, 75005, France.
authors.forename: Sudipta
authors.initials: S
authors.lastname: Ponra
authors.affiliation: LSO (UMR 7652), École Polytechnique - ENSTA ParisTech, Université Paris-Saclay , 91120, Palaiseau, France.
authors.forename: Aude
authors.initials: A
authors.lastname: Nyadanu
authors.affiliation: LSO (UMR 7652), École Polytechnique - ENSTA ParisTech, Université Paris-Saclay , 91120, Palaiseau, France.
authors.forename: Laurent El
authors.initials: LE
authors.lastname: Kaïm
authors.forename: Laurence
authors.initials: L
authors.lastname: Grimaud
authors.affiliation: PSL Research University , Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, Paris, 75005, France.
authors.forename: Maxime R
authors.initials: MR
authors.lastname: Vitale