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Cobaltocene cation monophosphine ligand and its synthesis and uses

A technology of cobaltocene cations and ions, which can be applied in organic compound/hydride/coordination complex catalysts, metallocenes, organic chemistry, etc., and can solve the problem of rare phosphine ligands

Inactive Publication Date: 2009-01-14
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Organophosphine ligands are widely used to catalyze various organic reactions, but phosphine ligands containing cobaltocene cation structures are rare

Method used

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  • Cobaltocene cation monophosphine ligand and its synthesis and uses
  • Cobaltocene cation monophosphine ligand and its synthesis and uses
  • Cobaltocene cation monophosphine ligand and its synthesis and uses

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of dicyclohexylphosphinocene cobalt hexafluorophosphate (expressed as I-1)

[0020] At -30°C, 0.0105 moles of dicyclohexylphosphine chloride (ClPCy 2 ), after stirring at room temperature for 1.5 hours, 0.0105 moles of n-butyl lithium was added dropwise to the reaction system at -78°C, returned to room temperature, and continued to stir for 1.5 hours. Add 0.0105 moles of cobalt chloride, the solution turns dark brown, and reflux overnight. Cool to room temperature, add 0.013 moles of hexachloroethane, the solution turns green, react for 10 minutes, remove the solvent under reduced pressure, dissolve the residue with 50 milliliters of dichloromethane, pass through a diatomaceous earth chromatographic column, and filter off lithium chloride. Obtain a green oil; dissolve the oil with dichloromethane, add 0.0105 moles of ammonium hexafluorophosphate aqueous solution, stir for 1 hour, no precipitation occurs; add an equal volume of water to the solution, then ex...

Embodiment 2

[0025] Preparation of diisopropylphosphinocene cobalt hexafluorophosphate (expressed as I-2)

[0026] At -30°C, add 0.0105 moles of diisopropylphosphine chloride (ClP(i-Pr) 2 ), after stirring at room temperature for 1.5 hours, 0.0105 moles of n-butyl lithium was added dropwise to the reaction system at -78°C, returned to room temperature, and continued to stir for 1.5 hours. Add 0.0105 moles of cobalt chloride, the solution turns dark brown, and reflux overnight. Cool to room temperature, add 0.013 moles of hexachloroethane, the solution turns green, react for 10 minutes, remove the solvent under reduced pressure, dissolve the residue with 50 milliliters of dichloromethane, pass through a diatomaceous earth chromatographic column, and filter off lithium chloride. Obtain a green oil; dissolve the oil with dichloromethane, add 0.0105 moles of ammonium hexafluorophosphate aqueous solution, stir for 1 hour, no precipitation occurs; add an equal volume of water to the solution, t...

Embodiment 3

[0031] Preparation of di-tert-butylphosphinocene cobalt hexafluorophosphate (expressed as I-3)

[0032] At -30°C, add 0.0105 moles of di-tert-butylphosphine chloride (ClP(t-Bu) 2 ), after stirring at room temperature for 1.5 hours, 0.0105 moles of n-butyl lithium was added dropwise to the reaction system at -78°C, returned to room temperature, and continued to stir for 1.5 hours. Add 0.0105 moles of cobalt chloride, the solution turns dark brown, and reflux overnight. Cool to room temperature, add 0.013 moles of hexachloroethane, the solution turns green, react for 10 minutes, remove the solvent under reduced pressure, dissolve the residue with 50 milliliters of dichloromethane, pass through a diatomaceous earth chromatographic column, and filter off lithium chloride. A green oil was obtained; the oil was dissolved in dichloromethane, and a 0.0105 mole aqueous solution of ammonium hexafluorophosphate was added, and stirred for 1 hour, but no precipitate was formed. Add an eq...

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Abstract

The invention relates to a cobaltocene cationic phosphine ligand (the general formula is I)and its synthesis and the application in Suzuki reaction (preparation of biphenyl with bromobenzene and borophenylic acid ) in catalytic ionic liquid, R represents cyclohexyl, isopropyl or tert-butyl group. The complex generated with said compound and palladium bichloride can effectively catalyze Suzuki coupling reaction with molar concentration of 1.0%.

Description

Technical field: [0001] The invention relates to a class of cobaltocene monophosphine ligands and their synthesis and application of complexes formed with palladium chloride in ionic liquids to catalyze Suzuki coupling reactions (reactions in which bromobenzene reacts with phenylboronic acid to form biphenyl). Background technique: [0002] Organophosphine ligands are widely used to catalyze various organic reactions, but phosphine ligands containing cobaltocene cation structures are rare. Ionic ligands can be dissolved in ionic liquids, but insoluble in less polar organic solvents, which is beneficial to the separation of products and catalysts. The present invention designs and synthesizes a class of monophosphine ligands containing dicyclocene cobalt cation structures, and uses such phosphine ligands to form complexes with palladium chloride in ionic liquids to catalyze Suzuki coupling reactions. Invention content: [0003] The purpose of the present invention is to ex...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02B01J31/24
Inventor 余广鳌刘盛华任勇
Owner HUAZHONG NORMAL UNIV
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