BiCl3-Mediated direct functionalization of unsaturated C–C bonds with an electrophilic SCF2PO(OEt)2 reagent

Jianjun Wang; Heng-Ying Xiong; Emilie Petit; Laëtitia Bailly; Xavier Pannecoucke; Thomas Poisson; Tatiana Besset

doi:10.1039/C9CC01851D

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BiCl₃-Mediated direct functionalization of unsaturated C–C bonds with an electrophilic SCF₂PO(OEt)₂ reagent†

Jianjun Wang,

^a Heng-Ying Xiong,

^a Emilie Petit,^a Laëtitia Bailly,^a Xavier Pannecoucke,

^a Thomas Poisson

^ab and Tatiana Besset

*^a

Author affiliations

* Corresponding authors

^a Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
E-mail: tatiana.besset@insa-rouen.fr

^b Institut Universitaire de France, 1 rue Descartes, 75231 Paris, France

Abstract

A transition metal-free approach was developed for the direct difunctionalization of disubstituted alkynes and terminal alkenes with concomitant formation of C–SCF₂PO(OEt)₂ and C–Cl bonds. The BiCl₃-mediated reaction offered access to high value-added functionalized scaffolds in a single operation under mild conditions. Extension to SCF₂PO(OEt)₂-containing alkynes was also studied.

This article is part of the themed collection: 2019 Emerging Investigators

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Article information

DOI: https://doi.org/10.1039/C9CC01851D
Article type: Communication
Submitted: 06 mar 2019
Accepted: 25 mar 2019
First published: 25 mar 2019

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Chem. Commun., 2019,55, 8784-8787

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BiCl₃-Mediated direct functionalization of unsaturated C–C bonds with an electrophilic SCF₂PO(OEt)₂ reagent

J. Wang, H. Xiong, E. Petit, L. Bailly, X. Pannecoucke, T. Poisson and T. Besset, Chem. Commun., 2019, 55, 8784 DOI: 10.1039/C9CC01851D

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