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A kind of synthetic method of fluorinated benzoheterocyclic-heteroaromatic ring structure

A compound and unsubstituted technology, applied in the field of synthesis of fluorobenzoheterocyclic-heteroaromatic rings, can solve problems such as poor compatibility of functional groups and lengthy reaction steps

Active Publication Date: 2018-01-23
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods usually have disadvantages such as lengthy reaction steps, poor functional group compatibility, and some reactions require the use of some highly toxic tin reagents.

Method used

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  • A kind of synthetic method of fluorinated benzoheterocyclic-heteroaromatic ring structure
  • A kind of synthetic method of fluorinated benzoheterocyclic-heteroaromatic ring structure
  • A kind of synthetic method of fluorinated benzoheterocyclic-heteroaromatic ring structure

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preparation example Construction

[0074] The invention provides a preparation method of fluorinated benzoheterocyclic-heteroaromatic ring and derivatives thereof. Preferably, the method comprises the steps of:

[0075] In an inert solvent, at a certain temperature (such as 40°C-140°C; preferably 60-100°C), using palladium salt as a catalyst, in the presence of an oxidizing agent, the compound of formula A (i.e. fluorobenzoheterocycle or Its derivative) reacts with the compound of formula B (ie heteroaromatic compound) for a period of time (such as 1-20 hours or 5-10 hours, etc.), thereby forming the compound of formula C (ie fluorobenzoheterocyclic-heteroaryl ring building blocks and their derivatives);

[0076]

[0077] In various forms, R 1 , R 2 , R' 1 , R' 2 , R' 3 , X, Y are defined as mentioned above.

[0078] Wherein, the compound of formula A is a compound selected from the following group:

[0079]

[0080] In various forms, R 1 , R 2 , R 5 as above.

[0081] More preferably, the com...

Embodiment 1

[0122]

[0123] In a three-neck flask, add compound 1 (compound 1 can be prepared with reference to US5514680A1, 5.6g, 25mmol), CHC1 3(150mL), triethylamine (11.4mL, 4equiv). After stirring for 15 minutes, thionyl chloride (SOCl 2 , 7.2g, 2equiv) was slowly dripped into it, and refluxed for 5h. Product 2 (5.1 g, 81% yield) was obtained as a white solid by column chromatography. 1 H NMR (300MHz, CDCl 3 )7.30(t,J=8.1Hz,1H). 19 F NMR (376MHz, CDCl 3 )-120.5(dd,J=19.9Hz,7.5Hz1F),-125.7(dd,J=19.7Hz,8.8Hz1F).

Embodiment 2

[0125]

[0126] 100 mL of H in HOAc (2.4 mL, 40 mmol) 2 O solution, add compound 3 to it, heat to dissolve it completely, after cooling to room temperature, slowly add NaNO 2 (1.52g dissolved in 20mL water) aqueous solution, and then filtered to obtain compound 4. Compound 4 (2.3g, 10mmol) was dissolved in 50mL of methanol, and tBuOK (1.15g, 1.02equiv) and C 8 h 17 Br (1.95g, 1.01 equiv). After reflux and stirring for 24 hours, the column was separated, and the colorless liquid compound 5 (1.20g, 35% yield) was remembered 1 H NMR (400MHz, CDCl 3 )7.55(dd,J=8.6Hz,7.0Hz,1H),4.70(t,J=7.4Hz,2H),2.10(m,2H),1.40-1.15(m,10H),0.86(t,J= 6.8Hz, 3H). 19 F NMR (376MHz, CDCl 3 )-128.9(dd,J=19.2Hz,6.8Hz1F),-129.7(dd,J=19.7Hz,8.8Hz1F).

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Abstract

The present invention relates to a kind of synthetic method of fluorinated benzoheterocycle-heteroaromatic ring structure, specifically, described method starts from simple fluorine-substituted benzoheterocycle and its derivatives and heteroaryl ring compounds, and the palladium Under the catalysis of salt, silver salt is used as oxidant to obtain various fluorine-substituted benzo-heterocyclic-heteroaromatic compounds in high yield. The method uses simple fluorine-substituted benzoheterocyclic and heteroaryl ring compounds as raw materials, and has the advantages of less catalyst consumption, wide application range of substrates, simple operation, high reaction efficiency and the like. The resulting fluorine-substituted benzoheterocyclic-heteroaromatic ring building blocks have a wide range of applications in organic semiconductors, optoelectronic materials and solar cells.

Description

technical field [0001] The invention belongs to the field of organic synthesis. Specifically, the present invention relates to a method for synthesizing a fluorobenzoheterocyclic-heteroaromatic ring. Background technique [0002] Fluorinated benzoheterocyclic-heteroaromatic rings play a very important role in organic electronic devices (such as organic light-emitting materials, optoelectronic materials, field-effect semiconductors, organic solar cells, etc.). However, in the traditional method of synthesizing fluorobenzoheterocyclic-heteroaromatic rings, usually by preactivated arene metal reagents (such as aryl boron compounds, aryl tin compounds, etc.) and halogenated fluorobenzoheterocyclic Prepared as starting material (for example, (a) Adv.Mater.2012,24,3646-3649; (b)J.Am.Chem.Soc.,2013,135(5),pp1806–1815; (c)J. Am.Chem.Soc., 2011, 133(12), pp4625–4631. However, these methods usually have disadvantages such as lengthy reaction steps, poor functional group compatibilit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14C07D487/04C07D495/04C07D409/04C07F9/6584
Inventor 张新刚贺春阳
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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