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Synthesis method for thiophene ring/furan ring-heteroaromatic ring structure

A compound and alkyl technology, applied in the field of chemistry, can solve problems such as poor compatibility of functional groups and lengthy reaction steps

Active Publication Date: 2013-04-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Synthesis method for thiophene ring/furan ring-heteroaromatic ring structure
  • Synthesis method for thiophene ring/furan ring-heteroaromatic ring structure
  • Synthesis method for thiophene ring/furan ring-heteroaromatic ring structure

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preparation example Construction

[0049]The present invention provides a method for preparing a thiophene ring / furan ring and its derivatives-heteroaromatic ring building blocks. Preferably, the method comprises the steps of:

[0050] 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 (ie thiophene ring or furan ring or Its derivative) reacts with the compound of formula B (ie heteroaromatic ring compound) for a period of time (such as 1-20 hours or 5-10 hours, etc.), thereby forming the compound of formula C (ie thiophene ring / furan ring and its derivatives -heteroaromatic ring building blocks);

[0051]

[0052] In various forms, R 1 , R 2 , R 3 , R' 1 , R' 2 , R' 3 , X, Y are defined as mentioned above.

[0053] Wherein, the compound of formula A is preferably a compound selected from the following group:

[0054]

[0055] In various forms, R 1 , R 2 , R ...

Embodiment 1

[0075]

[0076] Into a 25 mL reaction tube, add 6.7 mg (10 mol%) of Pd(OAc) 2 , AgOAc (0.9mmol), 2-N,N-dimethylformamidothiophene (0.3mmol, 1 equiv), nitrogen replacement three times and then add 2mL dimethylformamide (DMF), inject 87μL (0.45mmol)2 -Bromo-3-hexylthiophene, 30% yield after stirring at 80 °C for 8 hours.

Embodiment 2

[0078]

[0079] Into a 25 mL reaction tube, add 6.7 mg (10 mol%) of Pd(OAc) 2 , AgOAc (0.9mmol), 2-N,N-dimethylformamidothiophene (0.3mmol, 1 eq), nitrogen replacement three times, adding 2mL dimethylsulfoxide (DMSO), injecting 87μL (0.45mmol)2 -Bromo-3-hexylthiophene, after stirring at 80°C for 8 hours, the target compound was obtained by column separation with a yield of 28%.

[0080] 1 H NMR (300MHz, CDCl 3 )δ7.24(d,J=3.9Hz,1H),7.00(d,J=3.9Hz,1H),6.92(s,1H),3.19(s,6H),2.53(t,J=7.8Hz, 2H),1.57(m,2H),1.32(m,6H),0.89(t,J=6.6Hz,3H). 13 C NMR (75.4MHz, CDCl 3 )δ163.7, 143.1, 140.2, 136.4, 135.7, 130.0, 125.4, 122.9, 108.8, 31.5, 29.5, 29.4, 28.8, 22.5, 14.0.m.p.54°C.IR (thin film method): v max 3068,1610cm -1 .MS(EI):m / z(%)401(M + ),399(M + ), 274(100), 243, 171.HRMS: Calculated for (theoretical value): C 17 h 22 NOS 2 Br: 399.0326; Found (measured value): 399.0331.

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Abstract

The invention discloses a synthesis method for a thiophene ring / furan ring-heteroaromatic ring structure. Specifically, according to the synthesis method provided by the invention, various high-yield thiophene ring / furan ring-heteroaromatic ring building block compounds are prepared from thiophene ring or furan ring or derivatives thereof and heteroaromatic ring compounds in the prescence of palladium salt and oxidant. The synthesis method has the advantages of simple and readily available raw materials, small using amount of catalysts, wide application range of substrates, simplicity and convenience in operation, high reaction efficiency and the like. The prepared thiophene ring / furan ring-heteroaromatic ring building blocks are widely applied in the aspects of photoelectric materials, luminescent agents, solar batteries and the like.

Description

technical field [0001] The present invention belongs to the field of chemistry. Specifically, the present invention relates to a synthesis method of a thiophene ring / furan ring-heteroaryl ring building block. Background technique [0002] Thiophene ring / furan ring-heteroaromatic ring building blocks 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 thiophene ring / furan ring-heteroaromatic ring building blocks, it is usually prepared from pre-activated arene metal reagents (such as aryl boron compounds, aryl tin compounds, etc.) and halogenated arenes. (eg, (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. Wiley-VCH, Weinheim, 2004. (b) Cheng, Y.-J.; Yan, S. -H.;Hsu,C.-S.Chem.Rev.2009,109,5868.(c)Carsten,B.;He,F.;Son,H.-J.;Xu,T.;Yu,L . Chem. Rev. 2011, 111, 1...

Claims

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Application Information

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IPC IPC(8): C07D333/38C07D333/28C07D333/52C07D333/32C07D409/04C07D307/46C07D333/22
Inventor 张新刚贺春阳
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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