Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes

Sabrina Marie; Martin Lutz; Anthony L. Spek; Robertus J.M. Klein Gebbink; Gerard Van Koten; Nelly Kervarec; François Michaud; Jean-Yves Salaün; Paul-Alain Jaffres

doi:10.1016/j.jorganchem.2009.08.035

Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes

Sabrina Marie ¹ Martin Lutz ² Anthony L. Spek ² Robertus J.M. Klein Gebbink ² Gerard Van Koten ² Nelly Kervarec ³ François Michaud ⁴ Jean-Yves Salaün ¹ Paul-Alain Jaffres ¹

1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique

2 HU - University of Applied Sciences [Utrecht]

3 RMN-RPE-SM - Plateforme technologique de Résonance Magnétique Nucléaire et de Résonance Paramagnétique Electronique

4 PIMM-DRX - Centre Commun d’Analyse par Diffraction des Rayons X

Abstract : The O,O-diethyl thiophosphonate functional group has been introduced on position 2 of a pyrrole heterocycle following a two steps sequence that makes use of a [1,2] base-induced rearrangement applied for the first time to a O,O-diethyl thiophosphoramide intermediate. This rearrangement has been studied by low temperature NMR and the intermediates have been fully characterized. The coordination of this monoanionic bidentate (N,Ssp2) ligand to silver or palladium is studied The bidentate ligand 2 (O,O-diethyl pyrrol-2-ylthiophosphonate), associated with a palladium precursor, produces in the presence of triethylamine the complex trans-[Pd(η2-2′)2] 3 (2′ is deprotonated ligand 2). Ligand 2 also reacts with silver oxide in dichloromethane to give an unstable complex 2′-Ag that can be stabilized by addition of triphenylphosphine to produce the coordination complex 4 [Ag((η2-2′)(PPh3)2].

Keywords : Thiophosphonate Lithiation Rearrangement N S-ligand Pyrrole

Type de document :

Article dans une revue

Journal of Organometallic Chemistry, Elsevier, 2009, 694 (25), pp.4001 - 4007. 〈10.1016/j.jorganchem.2009.08.035〉

Domaine :

Chimie

Chimie / Chimie organique

Chimie / Cristallographie

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http://hal.univ-brest.fr/hal-01580243
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Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes

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Application of a base-induced [1,2]-rearrangement to synthesize thiophosphonate bidentate S(sp2)–N monoanionic ligand: Characterization of its silver and palladium complexes

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