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Aromatic boron compound of conjugated olefin as well as preparation method and application of aromatic boron compound

A technology of conjugated olefins and compounds, which is applied in the field of aromatic boron compounds of conjugated olefins and its preparation, can solve the problems of difficult control of olefin regioselectivity, and achieve good regioselectivity, high yield, and mild reaction conditions Effect

Pending Publication Date: 2022-08-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] However, the olefins used in the aromatic boron compound method for the synthesis of olefins can only be inert olefins, styrene, allenes, and alkynes. The main outstanding problems include: (1) for α,β-unsaturated olefins There are few reports on regioselective aromatic boron compounds. Only Nakao and Semba's research group studied the aromatic boronation of alkenes, and ethyl acrylate was used to obtain mixed aromatic boron compounds; (2) It is difficult to control the regioselectivity of alkenes addition.

Method used

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  • Aromatic boron compound of conjugated olefin as well as preparation method and application of aromatic boron compound
  • Aromatic boron compound of conjugated olefin as well as preparation method and application of aromatic boron compound
  • Aromatic boron compound of conjugated olefin as well as preparation method and application of aromatic boron compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] (1) Under an argon atmosphere, 0.2 mmol (about 57 mg) of conjugated olefin compound 2a, 0.6 mmol (about 152 mg) of pinacol biboronate, 0.01 mmol were sequentially added to a 25 mL Schlenk tube containing a magnetic stirring bar (about 3.7 mg) allylpalladium(II) chloride dimer, 0.02 mmol (about 9.4 mg) 2-dicyclohexylphosphine-2',6'-diisopropoxy-1,1'-bi Benzene, 0.6 mmol (about 82.9 mg) potassium carbonate, 0.3 mmol (about 32 uL) aryl bromide 1a (bromobenzene) were added to 2 mL of 1,4-dioxane, the tube was tightly capped, and the mixture was mixed In a preheated 100°C oil bath, vigorously stirring for 24 hours can complete the reaction;

[0082] (2) The reaction product was purified by silica gel column (triethylamine was used for silica gel, and PE:EA=2~20:1 as developing solvent) to obtain 77 mg of white conjugated olefin aryl boron compound 1 with a yield of 85 %.

[0083] Characterize compound 1 as Figures 1 to 2 shown, figure 1 its 1 H NMR nuclear magnetic spe...

Embodiment 2

[0090] (1) Under an argon atmosphere, 0.2 mmol of conjugated olefin compound 2a, 0.4 mmol of pinacol biborate, and 0.002 mmol of allyl palladium chloride were sequentially added to a dry 25 mL Schlenk tube containing a magnetic stirring bar. (II) dimer, 0.001 mmol 2-dicyclohexylphosphorus-2'-methylbiphenyl, 0.3 mmol potassium carbonate, 0.2 mmol aryl bromide 1c (p-tert-butylbromobenzene) was added to 2 mL tert-amyl alcohol , the tube was tightly capped, and the mixture was vigorously stirred in a preheated 80°C oil bath for 18 hours to complete the reaction;

[0091] (2) Purify the reaction product through silica gel column (use triethylamine for silica gel, and use PE:EA=2~20:1 as developing solvent) to obtain 100 mg of white conjugated olefin aryl boron compound 2 with a yield of 92 %.

[0092] Characterize compound 2 as Figures 3 to 4 shown, where, image 3 its 1 H NMR nuclear magnetic spectrum, Figure 4 its 13 CNMR nuclear magnetic spectrum.

[0093] The character...

Embodiment 3

[0099] (1) Under an argon atmosphere, 0.2 mmol of conjugated olefin compound 2a, 1 mmol of biboronic acid pinacol ester, 0.02 mmol of allyl palladium chloride ( II) dimer, 0.04mmol 2-dicyclohexylphosphorus-2'-methylbiphenyl, 0.8mmol potassium carbonate, 0.6mmol aryl bromide 1f (p-bromotrifluoromethoxybenzene) was added to 2mL 1, In 4-dioxane, the tube was tightly capped, and the mixture was vigorously stirred in a preheated 120°C oil bath for 36 hours to complete the reaction;

[0100] (2) Purify the reaction product through silica gel column (use triethylamine for silica gel, and use PE:EA=2~20:1 as developing solvent) to obtain 65 mg of white conjugated olefin aryl boron compound 3 with a yield of 57 %.

[0101] Compound 3 was characterized and the results were as follows Figures 5 to 7 shown, where, Figure 5 its 1 H NMR nuclear magnetic spectrum, Image 6 its 13 C NMR spectrum, Figure 7 its 19 F NMR nuclear magnetic spectrum.

[0102] The characterization data f...

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Abstract

The invention discloses an aromatic boron compound of conjugated olefin as well as a preparation method and application of the aromatic boron compound. The preparation method comprises the following steps: in an inert atmosphere, adding materials and a solvent into a reaction container, uniformly mixing, placing the reaction container in an oil bath at 80-120 DEG C, violently stirring and reacting for 18-36 hours to obtain a reaction product; the material comprises a conjugated olefin compound, an aryl bromide compound, bis (pinacolato) diboron, a palladium catalyst, a ligand compound and alkali. And purifying the reaction product to obtain the aromatic boron compound of the conjugated olefin. The preparation method has the characteristics of high yield, mild reaction conditions, simple reaction and post-treatment purification process, easiness in operation and the like, and the obtained compound has good regioselectivity, chemical selectivity and functional group compatibility and can be used for removing a guiding group 8-aminoquinoline in a 1, 6-dicarbonyl skeleton compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and particularly relates to an aromatic boron compound of a conjugated olefin and a preparation method and application thereof. Background technique [0002] Organoboron compounds are widely used in synthetic chemistry as synthetic building blocks, which can efficiently construct chemical bonds and effectively synthesize groups that are not easy to synthesize in other routes. For example, boron compounds (C-B) can be converted into cyano groups (C-CN). ), amino (C-NH 2 ), phenyl (C-Ar), halogen (C-X), etc. [0003] Olefins are cheap and easy to obtain, and are important raw materials for petrochemical and coal chemical industries. With the continuous development of science, the bifunctionalization (carbboration) of olefins has become a key topic in the field of organic chemistry. Existing synthetic strategies mainly involve the conversion of alkenes to alkyl borates by introducing two...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/18C07D215/40C07D307/33C07B53/00
CPCC07F5/025C07F7/1804C07F7/188C07D215/40C07D307/33C07B53/00C07B2200/09C07B2200/07Y02E10/549
Inventor 吴晓进周丽丽陈日志
Owner NANJING UNIV OF TECH
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