PNO ligand containing planar chiral ferrocene and application thereof

A chiral ferrocene and ligand technology, which is applied in the direction of metallocene, catalytic reaction, formation/introduction of hydroxyl groups, etc., can solve the problems of limited practical application value, poor ligand stability, expensive catalyst raw materials, etc., and achieve a large Large-scale production, easy synthesis, and good stability

Pending Publication Date: 2021-06-15
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The tridentate PNO ligands reported above need to use a variety of chiral sources. At the same time, the “OH” of the alkyl alcohol participates in the coordination of the ligands. Therefore, the raw materials for the synthesis of the catalyst are relatively expensive, and the synthesis efficiency is low. At the same time, the catalytic Low activity, limited substrate scope and reaction type
There are also some ligands that are less stable, thus limiting their practical application value

Method used

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  • PNO ligand containing planar chiral ferrocene and application thereof
  • PNO ligand containing planar chiral ferrocene and application thereof
  • PNO ligand containing planar chiral ferrocene and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1 contains the ligand of face chiral ferrocene (S FC )-L1 synthesis

[0053]

[0054] N 2 Under protection, a solution of n-butyllithium in n-hexane (12.4mL, 1.4M) was added dropwise to a solution of (S)-1 (3.6g, 14mmol) in anhydrous ether (20mL), and the reaction solution was kept at 0°C, and The dropping time was controlled for about 20 minutes to complete the dropping, and the reaction solution was stirred at room temperature for 1.5 hours, and then diphenylphosphine chloride (6.2 g, 28 mmol) in 10 mL of diethyl ether solution was slowly added dropwise to the reaction system. After the dropwise addition was completed, it was refluxed for 4h. Cool the reaction solution to room temperature, put it in an ice-water bath, slowly add a saturated aqueous solution of sodium bicarbonate dropwise, and extract the orange-yellow product with ether, combine the organic phases, wash with water, dry over anhydrous sodium sulfate, and dry in vacuo to obtain an orange...

Embodiment 2

[0062] Embodiment 2 contains the ligand of chiral ferrocene (S FC )-L8 synthesis

[0063]

[0064] Similar to the synthesis method of Example 1, at room temperature, under the protection of nitrogen, the synthesized compound (S,R)-4 (2.0g, 4.8mmol) was dissolved in absolute ethanol (15mL), and after being stirred to a homogeneous phase, the 2-Hydroxy-1-naphthaldehyde (0.91g, 5.3mmol) was added to the reaction system in batches, and the reaction was complete in about 6 hours. After the reaction was completed, an orange-red suspension was obtained. Then add NaBH to the suspension in batches at 0°C 4 Solid (0.46g, 12mmol), after the addition was completed, the reaction solution was raised to room temperature and stirred for 2h. After the reaction was monitored by TLC, it was quenched with water, extracted three times with DCM, and the organic phase was combined. The organic phase was washed with saturated brine, and finally washed with anhydrous Dry over sodium sulfate, remo...

Embodiment 3

[0065] Embodiment 3 contains the ligand of chiral ferrocene (S FC )-L15 synthesis

[0066]

[0067] Similar to the synthesis method of Example 1, at room temperature, under the protection of nitrogen, the synthesized compound (S,R)-4 (2.0g, 4.8mmol) was dissolved in absolute ethanol (15mL), and after being stirred to a homogeneous phase, the 3-tert-butyl salicylaldehyde (0.94g, 5.3mmol) was added to the reaction system in batches, and the reaction was complete in about 6 hours. After the reaction was completed, an orange-red suspension was obtained. Then add NaBH to the suspension in batches at 0°C 4 Solid (0.46g, 12mmol), after the addition was completed, the reaction solution was raised to room temperature and stirred for 2h. After the reaction was monitored by TLC, it was quenched with water, extracted three times with DCM, and the organic phase was combined. The organic phase was washed with saturated brine, and finally washed with anhydrous Dry over sodium sulfate, r...

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Abstract

The invention discloses a PNO ligand containing planar chiral ferrocene and application thereof. The PNO ligand containing planar chiral ferrocene is a planar chiral ferrocene-containing and phenol-containing PNO ligand as shown in a general formula (I) or (II) which is described in the specification, or a planar chiral ferrocene-containing and aryl-phosphoric-acid-containingPNO ligand containing as shown in a general formula (III) or (IV) which is described in the specification, or a planar chiral ferrocene-containing and carbon-chiral-phenol-containingPNO ligand as shown in a general formula (V) or (VI) which is described in the specification. The invention provides tridentate PNO ligands and processes for their complexation with transition metal salts or transition metal complexes; the introduction of salicylaldehyde and derivatives thereof, which are simple and easy to obtain, enables the ligands to have a bifunctionalization effect, and -OH in a formed catalyst has stronger acidity and is beneficial to combination with N/O in polar double bonds. Therefore, due to the bifunctionalization effect of the catalyst, the interaction between the catalyst and a substrate can be greatly improved, so a reaction can obtain higher catalytic activity and stereoselectivity.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a PNO ligand containing chiral ferrocene and an application thereof. Background technique [0002] Chiral compounds are widely used in medicine, food, materials, fine chemicals and other fields. Natural chiral compounds are far from meeting the needs of human beings. Therefore, it is important to develop green, efficient and highly selective catalytic reactions to prepare chiral compounds. theoretical and practical significance. According to the survey, in 2010, the global drug production value reached 880 billion US dollars, of which generic drugs reached 103 billion US dollars. Chiral drugs account for half of all drugs, however, as high as 85-90% of all chiral drugs are sold as racemates, chiral drugs with a single isomer have high application and commercial value, and recently Years have been extensively researched and developed. Therefore, it is necessary to explor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02B01J31/24C07C29/145C07C37/00C07D213/30C07D233/64C07D307/44C07C33/22C07C35/21C07C39/11C07C33/46C07B41/02
CPCC07F17/02B01J31/2409C07C29/145C07C37/002C07D213/30C07D233/64C07D307/44C07B41/02B01J2531/827B01J2531/822B01J2531/72B01J2531/824B01J2531/847B01J2231/643C07C2601/14C07C33/22C07C35/21C07C39/11C07C33/46
Inventor 武卫龙吉保明亢国辉
Owner LUOYANG NORMAL UNIV
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