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(2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenyl phosphine ligand and preparation method thereof

A technology of trifluoromethyl and phenylphosphine, which is applied in the field of organochemical metal-catalyzed ligand synthesis, can solve the problems of limited application, unfavorable reduction and elimination of electron-rich ligands, etc., and achieves simple operation, rich synthesizable structures, and easy raw materials The effect

Inactive Publication Date: 2017-12-01
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Since the electron-rich ligand is not conducive to the reductive elimination of the reaction, it limits its application in palladium-catalyzed specific substrate reactions

Method used

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  • (2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenyl phosphine ligand and preparation method thereof
  • (2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenyl phosphine ligand and preparation method thereof
  • (2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenyl phosphine ligand and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0082] Preparation of (2-(2,4,6-triisopropylphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine

[0083] a) Preparation of 2-(2,4,6-triisopropylphenyl)indene: 3 mmol of 2-bromoindene (Shanghai Beide Pharmaceutical Technology Co., Ltd.) , 1.5mmol of 2,4,6-triisopropylphenylboronic acid (Shanghai Beide Pharmaceutical Technology Co., Ltd.), 3mmol% of palladium acetate, 6mmol% of S-Phos and 3mmol of potassium phosphate, add 20mL of tetrahydrofuran and 10mL of water The mixture to dissolve the reactants was reacted at 100°C for 24 hours. After cooling, the reaction solution was extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, the organic phase solvent was removed, and column chromatography was carried out with petroleum ether as a developing solvent (Rf=0.8) to obtain 2-(2,4,6- Triisopropylphenyl) indene, the yield is 85%.

[0084] b) Preparation of (2-(2,4,6-triisopropylphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine:...

Embodiment 2

[0086] Preparation of (2-(2,4,6-trimethylphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine

[0087] a) Preparation of 2-(2,4,6-trimethylphenyl)indene: under an argon atmosphere, in a Schlenk bottle, 3 mmol of 2-bromoindene (Shanghai Biide Pharmaceutical Technology Co., Ltd.), 1.5mmol of 2,4,6-trimethylphenylboronic acid (Shanghai Beide Pharmaceutical Technology Co., Ltd.), 3mmol% of tetrakistriphenylphosphine palladium, 6mmol% of S-Phos and 3mmol of potassium phosphate, add 20mL of toluene and 10 mL of water to dissolve the reactants. React at 100°C for 24 hours, extract the reaction solution with ethyl acetate after cooling, dry the organic phase with anhydrous sodium sulfate, remove the organic phase solvent, and perform column chromatography with petroleum ether as a developing solvent (Rf=0.8) to obtain 2 -(2,4,6-trimethylphenyl)indene, the yield is 90%.

[0088]b) Preparation of (2-(2,4,6-trimethylphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine: ...

Embodiment 3

[0090] Preparation of (2-(2,6-dimethoxyphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine

[0091] a) Preparation of 2-(2,6-dimethoxyphenyl)indene: under an argon atmosphere, in a Schlenk bottle, 3 mmol of 2-bromoindene (Shanghai Beide Pharmaceutical Technology Co., Ltd.), 1.5 Mmol of 2,6-dimethoxyphenylboronic acid (Shanghai Beide Pharmaceutical Technology Co., Ltd.), 3mmol% of palladium acetate, 6mmol% of S-Phos and 3mmol of potassium phosphate were added to a mixture of 20mL THF and 10mL water to dissolve Reactant. React at 100°C for 24 hours, extract the reaction solution with ethyl acetate after cooling, dry the organic phase with anhydrous sodium sulfate, remove the organic phase solvent to dryness, and perform column chromatography with petroleum ether as a developing solvent (Rf=0.8) to obtain 2 -(2,6-dimethoxyphenyl)indene, the yield is 79%.

[0092] b) Preparation of (2-(2,6-dimethoxyphenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenylphosphine: under argo...

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Abstract

The invention relates to large-steric-hindrance electron-deficient organic phosphine ligands and more specifically relates to a (2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl))phenyl phosphine ligand compound with a structure shown as a formula and a synthesis method thereof. The large-steric-hindrance electron-deficient organic phosphine ligand compound provided by the invention has many modifiable sites, abundant synthesizable structures and stable properties, and can exist stably in the air; raw materials are easy to obtain, and the operation is simple and convenient; the large-steric-hindrance electron-deficient organic phosphine ligand compound can be used as an important ligand in the field of a palladium catalyst. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the field of organochemical metal-catalyzed ligand synthesis and relates to large-site-blocking electron organophosphine ligand compounds, especially (2-(substituted phenyl)indenyl)-bis(3,5-bis(trifluoromethyl) )) Phenylphosphine ligand compound and preparation method thereof. Background technique [0002] Organophosphine ligands have always been an indispensable and important ligand in the field of palladium catalysis, and its development is an important reason for many breakthroughs in palladium-catalyzed reactions. [0003] In 2013, the Biscoe research group found that the biaryl phosphine ligand JackiePhos can efficiently catalyze the reaction in the palladium-catalyzed stille reaction of the secondary alkyl cage tin and aryl halide, with mild reaction conditions and a wide range of substrates. Stereo-configuration retention (see: Li L, Wang C Y, Huang R, et al.Stereoretentive Pd-catalysed Stillecross-coupling reactions of...

Claims

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Application Information

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IPC IPC(8): C07F9/50C07F15/00B01J31/24
CPCC07F9/5022B01J31/2404B01J2231/4205B01J2531/0258B01J2531/824C07F9/5068C07F15/006
Inventor 肖斌周巧兰徐梦雨
Owner UNIV OF SCI & TECH OF CHINA
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