title: Copper-Mediated Formation of Aryl, Heteroaryl, Vinyl and Alkynyl Difluoromethylphosphonates: A General Approach to Fluorinated Phosphate Mimics.
abstract: A general and efficient access to aryl, heteroaryl, vinyl and alkynyl difluoromethylphosphonates is described. The developed methodology using TMSCF2PO(OEt)2, iodonium salts and a copper salt provided a straightforward manifold to reach these highly relevant products. The reaction proved to be highly functional group tolerant and proceeded under mild conditions, giving the corresponding products in good to excellent yields. This method represents the first general synthetic route to this important class of fluorinated scaffolds, which are well-recognized as in vivo stable phosphate surrogates.
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France).
authors.forename: Maria V
authors.initials: MV
authors.lastname: Ivanova
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France).
authors.forename: Alexandre
authors.initials: A
authors.lastname: Bayle
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France).
authors.forename: Tatiana
authors.initials: T
authors.lastname: Besset
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France). thomas.poisson@insa-rouen.fr.
authors.forename: Thomas
authors.initials: T
authors.lastname: Poisson
authors.affiliation: Normandie Univ., COBRA, UMR 6014 et FR 3038, Univ. Rouen, INSA Rouen, CNRS, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex (France).
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
keywords: copper; fluorine; iodonium salts; phosphate mimic; synthetic method