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Ferrocenyl pyrimidine pincer ligand and preparation method thereof

A ferrocene-based pyrimidine clamp and base pyrimidine clamp technology are applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., to achieve the effects of good thermal stability, mild reaction conditions and high yield

Inactive Publication Date: 2015-06-03
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing clamp ligands usually have a symmetrical structure, that is, the groups connected to the 2-position and 6-position of the aryl group are the same, and it is still difficult to obtain an asymmetric clamp ligand. Pincer ligands have not been reported

Method used

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  • Ferrocenyl pyrimidine pincer ligand and preparation method thereof
  • Ferrocenyl pyrimidine pincer ligand and preparation method thereof
  • Ferrocenyl pyrimidine pincer ligand and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The ferrocenyl pyrimidine pincer ligand has the following general formula: Its specific structure can be:

[0021]

[0022]

Embodiment 2

[0024] The preparation method of ferrocenyl pyrimidine pincer ligand, the steps comprise:

[0025]

[0026] Wherein, the possible structure of intermediate B and its corresponding product number are as follows:

[0027]

[0028]

[0029]

[0030] The preparation process of the specific product is described in detail below.

[0031] 2.1 Preparation method of ferrocenyl pyrimidine pincer ligand (1)

[0032] Step (1): Synthesis of Intermediate A

[0033] Under the protection of high-purity nitrogen, add 0.5mmol of 2,4,6-trichloropyrimidine, 0.6mmol of ferrocene mercuric chloride, and 0.005mmol of tetrakis(triphenylphosphine)palladium to a 10ml Schlek reaction tube, and replace the reaction with nitrogen Tube 3 times, and inject 5ml of tetrahydrofuran solvent with a syringe under the continuous protection of slight positive pressure nitrogen, then heat to 80°C with an oil bath under magnetic stirring, and reflux for 10 hours.

[0034] Remove the oil bath, and lower ...

Embodiment 3 2

[0117] Embodiment 3 The purposes of ferrocenyl pyrimidine pincer ligand

[0118] Synthesis of palladium catalyst—compound (21) using ferrocenyl pyrimidine pincer ligand (5):

[0119]

[0120] Under the protection of nitrogen, add 1 mmol of ferrocenyl pyrimidine pincer ligand (5), 1.2 mmol of PdCl2 and 10 ml of acetic acid into a 10 ml Schlek reaction tube, replace the reaction tube with nitrogen for 3 times, and then use an oil bath under magnetic stirring Heated to 120°C and refluxed for 24 hours. The resulting red solid was filtered off and dried to obtain the ferrocenyl pincer-shaped palladium compound (21) with a yield of 82%. The nuclear magnetic analysis data of this product are as follows: 1 H NMR. (400MHz, CDCl 3 ):δ8.71(s,1H,PyH),7.78(d,1H,PyH),7.55(d,1H,PyH),7.51(s,1H,PyH),7.47(d,1H,ArH),7.26 (d,1H,ArH),7.20(d,1H,ArH),5.13(s,2H,C 5 h 4 ),4.56(s,2H,C 5 h 4 ),4.11(s,5H,C 5 h 5 ),2.37(s,3H,CH 3 ),2.32(s,3H,CH 3 ).

[0121] Compound (21) can be used as a ...

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Abstract

The invention discloses a ferrocenyl pyrimidine pincer ligand and a preparation method thereof and belongs to the technical field of organic synthesis. The ferrocenyl pyrimidine pincer ligand has the general formula shown in the specification, wherein X and Y are atom C or N; R1 and R2 are C1-C6 linear alkyl, -C6H5, -COCH3, -COOCH3, -CHO, -OCH3, -N(CH3)2, -CN or -COOH; R1 is connected to the ortho-position, meta-position or para-position of X; and R2 is connected to ortho-position, meta-position or para-position of Y. According to the corresponding preparation method, 2,4,6-trichloro pyrimidine, ferrocene mercuric chloride, aryl or heterocyclic aryl boric acid serve as raw materials, and the ferrocenyl pyrimidine pincer ligand of a rich structure is prepared through a stepped coupling method. The preparation method is mild in reaction conditions, wide in substrate range and high in yield. The selected raw material ferrocene mercuric chloride has high stability and high stereoselectivity in air and water, the compound can be prepared by directly mercurating ferrocene, and the operation is easy and readily available. Meanwhile, multiple asymmetric pincer structures can be conveniently obtained by utilizing the preparation method, and the ligand has wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a class of ferrocenyl pyrimidine pincer ligands, and also relates to a synthesis method of such compounds. Background technique [0002] Ferrocene is a typical representative of metallocene compounds due to its special structure and properties, and has important theoretical value and broad application prospects. The research work on the synthesis, structure and properties of ferrocene and its derivatives has been very active. These studies have promoted the development of chemical bond theory and structural chemistry, expanded the scope of metal organic chemistry, and are milestones in the development of metal organic chemistry. [0003] Pincer ligands refer to a class of compounds that contain structures similar to the following: That is, an atomic group containing an electron donor is introduced at the 2 and 6 positions of the aryl group, and the electron...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02B01J31/22C07C67/343C07C69/618
Inventor 李红梅徐晨王志强李仕辉娄新华
Owner LUOYANG NORMAL UNIV
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