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A method for fluoroalkylation of aromatics or heteroaromatics under acetone induction
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A technology for fluoroalkylation and heteroaromatics, applied in the field of organic synthesis, can solve problems such as poor functional group compatibility and expensive catalysts, and achieve high-efficiency synthesis, excellent functional group compatibility, and excellent reaction diversity.
Active Publication Date: 2020-11-03
ZUNYI MEDICAL UNIVERSITY
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[0007] The present invention intends to provide a novel method for the fluoroalkylation of aromatic or heteroaromatic compounds to solve the problems of poor functional group compatibility or the need to use expensive catalysts and catalyst ligands in the synthesis of such compounds in the prior art
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[0027] The invention provides a method for synthesizing fluoroalkyl-substituted aromatic hydrocarbons, heteroaromatic hydrocarbons and derivatives thereof. Preferably, the method includes the steps of: at a certain temperature, under the irradiation of visible light, using acetone as a solvent and an electron donor compound, while adding DMF (N,N-dimethylformamide) or DMA (N,N -dimethylacetamide) as a co-solvent, in the presence of a base, the compound of formula A / compound of formula B / compound of formula C / compound of formula D is reacted with the compound of formula E to form compound of formula F / compound of formula G / compound of formula H compound / compound of formula I;
[0028]
[0029] In various forms, R 1 , R 2 , R 3 , R 4 , R f Defined as above.
[0030] More preferably, the compound of formula A / compound of formula B / compound of formula C / compound of formula D is an aromatic hydrocarbon or a heteroaromatic hydrocarbon, selected from the compounds of the fol...
Embodiment 1-7
[0043]
[0044] Into a 25mL reaction tube, add the following bases (0.60mmol), replace with argon three times, add 1mL acetone (Acetone) + 1mL N,N-methylformamide (DMF), inject 29μL (0.30mmol, 1 equivalent) of the compound B-2, 66 μL (0.45 mmol) of compound E-1 was stirred under blue lightirradiation for 24 hours to obtain compound G-2 with the following yield (fluorine spectrum yield). 1H NMR (400MHz, CDCl 3 )δ7.18-7.16(m,1H),6.72-6.69(m,1H),4.35(q,J=7.2Hz,2H),2.51-2.49(m,3H),1.35(t,J=7.2Hz ,3H). 19 F NMR (376MHz, CDCl 3 )δ-92.9(s,2F).
[0045] Table 1
[0046]
[0047]
Embodiment 8-11
[0049]
[0050] To a 25mL reaction tube, add Na 2 CO 3 (63.6mg, 0.60mmol), after argon replacement three times, add 2mL of the following solvent (v:v=1:1), inject 29μL (0.30mmol, 1 equivalent) of compound B-2, 66μL (0.45mmol) of compound E-1 , after stirring for 24 hours under blue light irradiation, compound G-2 was obtained with the following yield (fluorine spectrum yield). 1 H NMR (400MHz, CDCl 3 )δ7.18-7.16(m,1H),6.72-6.69(m,1H),4.35(q,J=7.2Hz,2H),2.51-2.49(m,3H),1.35(t,J=7.2Hz ,3H). 19 F NMR (376MHz, CDCl 3 )δ-92.9(s,2F).
[0051] Table 2
[0052]
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Abstract
The invention discloses a method for fluoroalkylation of aromatic hydrocarbons or heteroaromatic hydrocarbons under acetone induction, belonging to the technical field of organic synthesis. Specifically, aromatic hydrocarbons or heteroaromatic hydrocarbons which are simple and easily available and an iodofluoroalkyl compound are used as raw materials; under the irradiation of visible light, cheapand green acetone is innovatively selected as a main solvent and an electron donor compound, and DMF (N,N-dimethylformamide) or DMA (N,N-dimethylacetamide) is added as a cosolvent at the same to so asto realize high-yield preparation of various fluoroalkyl-substituted aromatic hydrocarbons and heteroaromatic hydrocarbons thereof. The method has the advantages of a simple reaction system, excellent atom economy and excellent functional group compatibility.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for fluoroalkylating aromatics or heteroaromatics under the induction of acetone. Background technique [0002] Due to the special properties of fluorine, fluorine-containing organic compounds are widely used in life science, biomedicine, and material science. Therefore, the development of efficient and concise new methodology for the synthesis of fluorine-containing organic compounds is the current key research direction of organofluorine chemistry. [0003] Aromatics and heteroaromatics are a class of common and very important compounds, and their fluoroalkylated products have very important applications in medicinal chemistry. Usually, the synthesis of this structure is achieved by the presence of transition metal catalysts or photocatalysts as shown in Formula 1. [0004] [0005] Formula 1: A method for the fluoroalkylation of aromatics and heteroarom...
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