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Phosphaalkenes palladium(II) complexes in the suzuki and sonogashira cross-coupling reactions^†

Bernard Deschamps

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Xavier Le Goff,

Xavier Le Goff

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Louis Ricard,

Louis Ricard

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Pascal Le Floch,

Corresponding Author

Pascal Le Floch

[email protected]

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, FranceSearch for more papers by this author

Bernard Deschamps,

Bernard Deschamps

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Xavier Le Goff,

Xavier Le Goff

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Louis Ricard,

Louis Ricard

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

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Pascal Le Floch,

Corresponding Author

Pascal Le Floch

[email protected]

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, France

Département de Chimie, Ecole Polytechnique, Laboratoire 〈〈Hétéroéléments et Coordination〉〉, UMR CNRS 7653, 91128 Palaiseau Cédex, FranceSearch for more papers by this author

First published: 02 May 2007

https://doi.org/10.1002/hc.20307

Citations: 22

^†

For further details on the theoretical structure of complexes I and II and the X-ray structural data for complexes 4 and 5, contact Pascal Le Floch.

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Abstract

The 1-methoxy-2-(supermesitylphosphanylidenemethyl)-benzene ligand (1) was prepared by reacting the phospha-Wittig reagent [Mes*PPMe₃] with o-methoxybenzaldehyde. Reaction of 1 with one equivalent of the [Pd(allyl)Cl]₂ dimer in the presence of Ag(OTf) affords a neutral complex (4) in which the triflate ligand is coordinated to the palladium atom. DFT calculations show that the formation of complex 4 is favored by 22.4 kcal/mol with respect to that of a chelate species involving coordination of the ligand through the phosphorus atom of one lone pair at the oxygen of the pendant methoxy group. Reaction of two equivalents of ligand 1 with the [Pd(allyl)Cl]₂ dimer affords complex 5, in which the two ligands are coordinated through their phosphorus atom. The catalytic activity of complex 5 was compared to that of the 1,3-bis[2-(supermesityl)phosphanediylmethyl]benzene palladium chloride complex (6). Performances of the two catalysts were found to be similar in the Suzuki cross-coupling reaction between phenylboronic acid and some arylbromides (TON between 55.10⁵ and 99.10⁵) as well as in the Sonogashira coupling between phenylacetylene and arylbromides (TON between 400 and 950). © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:363–371, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20307

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Phosphaalkenes palladium(II) complexes in the suzuki and sonogashira cross-coupling reactions^†

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Phosphaalkenes palladium(II) complexes in the suzuki and sonogashira cross-coupling reactions†

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Phosphaalkenes palladium(II) complexes in the suzuki and sonogashira cross-coupling reactions^†