Synthesis method of boron-nitrogen benzocarbazole derivative

A technology of benzocarbazole and synthesis method, which is applied in the field of synthesis of borazine benzocarbazole derivatives, can solve the problems of cumbersome post-processing, harsh reaction conditions, and difficulty in realizing the synthesis of boron-nitrogen skeletons with novel structures.

Pending Publication Date: 2021-05-11
JIUJIANG SHANSHUI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] (c) Electrophilic borylation reaction (CN1130396109A; Dalton Trans. 2016, 45 ,5920; Angew. Chem. Int. Ed .,2012, 51 , 6074.) is currently the mainstream method for synthesizing boron-nitrogen-containing aromatic compounds. This type of method has relatively large limitations. Boron atoms are introduced in the last step, and relatively sensitive boron-bromine compounds are used, and there are harsh reaction conditions and raw materials. Instability,

Method used

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  • Synthesis method of boron-nitrogen benzocarbazole derivative
  • Synthesis method of boron-nitrogen benzocarbazole derivative
  • Synthesis method of boron-nitrogen benzocarbazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027]Example 1

[0028]Synthetic compound:

[0029]

[0030]The 2L dry three-neck flask was taken, and the argon was evacuated 3 times. Under nitrogen protection, the o-aminostyrene (14.4 g, 0.12 mol), potassium phenyloborate (26.2 g, 0.1 mol), four Silicon chloride (17.0 g 0.1 mol), aniline (9.5 g, 0.12 mol), double (dibenzyl acetone) palladium (575 mg, 1 mol%), 2-bicyclic phosphorus-2 ', 4', 6 ' - Triisopropylbin (952 mg, 2 mol%), tert-butoxide (11.5 g, 0.12 mol), introduced anhydrous oxygen-free solvent toluene (500 mL). Under argon, the reaction was at 100 ° C for about 8 h, the reaction ended, and the temperature of the treatment was reduced to room temperature, ethyl acetate (4 * 1L) and water (2L) were extracted, dried, and the crystal crystal was 25.6 g, yield 87 %.

[0031]The nuclear magnetic analysis data of the compound is as follows:

[0032]1H NMR (400 MHz, CDCL3: δ 8.63 (1H, S,NH ), 8.42 (1H, S), 8.23 ​​(1H, D,J= 12 Hz), 7.82 (2H, T,J= 8 Hz), 7.48-7.69 (3H, M), 7.22-7.36 (7H, M).13...

Example Embodiment

[0033]Example 2

[0034]Synthetic compound:

[0035]

[0036]The 2L dry three-neck flask was taken, and the argon was evacuated 3 times. Under nitrogen protection, the o-aminostyrene (14.4 g, 0.12 mol), potassium phenyloborate (26.2 g, 0.1 mol), four Silicon chloride (17.0 g 0.1 mol), pair methoxyenine (14.8 g, 0.12 mol), bis (dibenzyl acetone) palladium (290 mg, 0.5 mol%), 2-bicyclic phosphorus-2 ', 4 ', 6'-triisopropylbenzene (480 mg, 1 mol%), tert-butanol sodium (11.5 g, 0.12 mol), introduced into anhydrous oxygen-free solvent toluene (500 mL). Under argon, the reaction was at 80 ° C for about 4 h, the reaction ended, and the temperature of the treatment was reduced to room temperature, ethyl acetate (4 * 1L) and water (2L) were extracted, combined with organic phases, sodium anhydrous sodium sulfate, recrystallization The white solid was 26.9 g, and the yield was 83%.

[0037]The nuclear magnetic analysis data of the compound is as follows:

[0038]1H NMR (400 MHz, CDCL3: δ 8.56 (1H, S,NH ), 8...

Example Embodiment

[0039]Example 3

[0040]Synthetic compound:

[0041]

[0042]The 2L dry three-neck flask was taken, and the argon was evacuated 3 times. Under nitrogen protection, o-aminostyrene (14.4 g, 0.12 mol), potassium phenyloborate (26.2 g, 0.1 mol), four Silicon chloride (17.0 g 0.1 mol), trifluoromethylideine (19.4 g, 0.12 mol), chloride-olycene (II) dimer (183 mg, 0.5 mol%), 2- (Dirt-D-D-D-D-D-D-D-D-D-D-D-D-D-D-D-D-D-Der Carnate (298 mg, 1 mol%), tert-butoxide (11.5 g, 0.12 mol), introduced in anhydrous oxygen-free solvent tetrahydrofuran (500 mL). Under argon, at 60 ° C reacted about 8 h, the reaction ended, and the temperature of the treatment was reduced to room temperature, ethyl acetate (4 * 1L) and water (2L) were extracted, combined with organic phase, sodium anhydrous sodium sulfate, and dry The crystalline was crystallized to 28.2 g, and the yield was 78%.

[0043]The nuclear magnetic analysis data of the compound is as follows:

[0044]1H NMR (400 MHz, CDCL3: δ 8.89 (1H, S,NH ), 8.51 (1H, S), ...

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Abstract

A synthesis method of a boron-nitrogen benzocarbazole derivative comprises the following steps: adding an o-amino styrene derivative, an aryl fluoroborate derivative, ammonia gas or organic amine, and a composite catalyst into a solvent in a nitrogen atmosphere, conducting heating to 25-100 DEG C, conducting reacting for 1-24 hours, and extracting, drying and recrystallizing the product to obtain the boron-nitrogen benzocarbazole derivative. In terms of per millimole of the aryl fluoborate derivative, the amount of the solvent is 5 mL, the amount of the o-amino styrene derivative is 1.2-1.5 mmol, the amount of the ammonia gas or the organic amine is 0.35-6 mmol, the amounts of the organic palladium and the phosphine compound are respectively 0.5-10% and 1-20% of the mole percentage of the aryl fluoborate derivative, and the amount of the alkaline compound is 1-6 mmol. The method is mild in reaction condition, wide in raw material application range, high in reaction specificity, high in yield and small in environmental pollution.

Description

technical field [0001] The invention relates to a synthesis method of boron nitrogen benzocarbazole derivatives, and specifically belongs to the technical field of synthesis of boron nitrogen aromatic compounds. Background technique [0002] Organic conjugated materials with photoelectric activity have become one of the current research and development hotspots because of their broad application prospects in organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs), organic solar cells (OPVs) and organic sensors. one. Designing and synthesizing organic functional materials with new structures is of great significance to the improvement of the performance of organic electronic devices, and promotes the development of organic electronics from the source. Organic functional materials are mostly small molecules or polymers with π-conjugated structures. By adjusting the molecular structure and intermolecular interactions, the electronic structure and three...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02Y02E10/549Y02P20/584
Inventor 黄国荣吴秀荣柳艳清聂锋黎祖国黄华南
Owner JIUJIANG SHANSHUI TECH
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