CN111517903A - Aromatic C-NO catalyzed by transition metal2Hiyama coupling method of - Google Patents
Aromatic C-NO catalyzed by transition metal2Hiyama coupling method of Download PDFInfo
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- CN111517903A CN111517903A CN202010391498.4A CN202010391498A CN111517903A CN 111517903 A CN111517903 A CN 111517903A CN 202010391498 A CN202010391498 A CN 202010391498A CN 111517903 A CN111517903 A CN 111517903A
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- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
- C07C1/323—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a nitrogen atom
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- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
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- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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Abstract
The invention provides a transition metal catalyzed aromatic C-NO2The Hiyama coupling method is to use aromatic C-NO in an organic solvent under the protection of nitrogen2And an organic silicon reagent is taken as a substrate, cross coupling reaction is carried out under the action of alkali through the action of a transition metal catalyst and a ligand, and the aromatic compound is obtained through a column chromatography or recrystallization method. The method has the advantages of low synthesis operation difficulty, simple post-treatment, high conversion rate, good substrate universality and the like, can construct a series of aromatic compounds, and has application prospects in the fields of medicines, chemical industry and materials.
Description
Technical Field
The invention belongs to the technical field of organic catalytic synthesis, and particularly relates to aromatic C-NO catalyzed by transition metal2The Hiyama coupling method of (1).
Background
Transition metal catalyzed coupling reactions are among the most efficient and commonly used synthetic methods for the construction of carbon-carbon (hetero) bonds. Conventional coupling reactions typically involve (quasi) halogenated aromatic hydrocarbons as electrophilic coupling components, which undergo various coupling reactions with metal reagents, nucleophiles, alkenes, or alkynes, to form various carbon-carbon or carbon-heterobonds [ j. Furthermore, aryl diazonium salts [ chem.rev.,2006,106,4622 ], aryl hydrazines [ chi.j.org.chem., 2016,36,1790], aromatic carboxylic acids [ j.chem.soc.rev.,2011,40,5030] and aromatic sulfinic acids [ eur.j.org.chem.,2016,408; chem. -eur. j.,2016,22,8663] was also used as an electrophilic coupling component, participating in a variety of coupling reactions. Although the electrophilic coupling components described above have been widely used in coupling reactions, it would be of great interest to develop more efficient, inexpensive and readily available electrophilic components.
The aromatic nitro compound is an important raw material for preparing aromatic compounds, has wide source and low price, is a precursor of energetic compounds, and can be used as a new electrophile to replace halogenated aromatic hydrocarbon. Transition metals catalyze the Suzuki cross-coupling reaction of aryl nitro compounds (Angew. chem., Int.Ed.,2000,112,974; Angew. chem., Int.Ed.,2006,45, 2720; J.Am.chem.Soc.,1982,104,3727; Org.Lett.,2013,15, 3966; Org.Lett.,2011,13, 1726; Chin.J.Org.chem.,2016,36, 1021; RSC adv.,2016,6, 33380; Eur.J.Org.Chem., 387, 2; Catal.Commun.,2017,94, 33; J.Am.chem.Soc.,2017,139,9423; Angew.chem., Int.Ed.,2017,56, 13307; Catal.399, Org.Lett.4839, 21,4721; Angel.78; No. 7-Flex-Doct.C., No. 35; No. 2, No. 7, No. 3, No. 25, No. 2, No. 3, No.. Thus developing transition metal catalyzed aromatic C-NO2It is particularly important to carry out cross-coupling reactions with other nucleophiles.
Disclosure of Invention
Technical problem to be solved
The invention provides a transition metal catalyzed aromatic C-NO2The Hiyama coupling method aims at solving the technical problems of simplifying operation and improving reaction yield.
(II) technical scheme
In order to solve the technical problem, the invention provides a transition metal catalytic aromatic C-NO2The Hiyama coupling method of (1), the coupling method comprising: in an organic solvent under nitrogen atmosphere, using aromatic C-NO2And an organic silicon reagent as a substrate, performing cross coupling reaction under the action of alkali through the action of a transition metal catalyst and a ligand, and obtaining an aromatic compound through methods such as column chromatography or recrystallization; aromatic C-NO2The structural formula of (A) is: Ar-NO2(I) Wherein Ar is phenyl, substituted phenyl, naphthyl, heteroaryl or substituted heteroaryl; the structural formula of the organosilicon reagent is as follows: R-SiX3(II) wherein R is phenyl, substituted phenyl, heteroaryl or substituted heteroarylX is fluorine, methyl, methoxy or ethoxy; the cross-coupling reaction equation is as follows:
further, in the formula (I), the substituted phenyl is alkyl, alkoxy, morphinyl, ester group, nitro, fluorine, phenyl substituted by trifluoromethyl; the aromatic group is a nitrogen-containing aromatic group; in the formula (II), the substituted phenyl is alkyl, alkoxy, trifluoromethyl, ester group, dimethylamino and cyano-substituted phenyl.
Furthermore, the nitrogen-containing aryl hetero group is pyridine, quinoline, isoquinoline or indole aryl hetero group.
Further, the transition metal catalyst is Pd (acac)2、Pd(OAc)2、PdCl2、Pd(CH3CN)2Cl2、Pd(PPh3)2Cl2、Pd(dppf)Cl2、Pd2(dba)3、Pd(TFA)2、Pd2(allyl)2Cl2、Ni(COD)2、NiCl2(PCy3)2Any one of them.
Further, the ligand is Brettphos, SPhos, IPr, IMes, SIMes, XPhos, RuPhos, PtBu3Any one of DPPF and BINAP.
Further, the organic solvent is any one of dioxane, toluene, tetrahydrofuran, N-dimethylformamide, isopropanol, ethanol, ethylene glycol or ethylene glycol dimethyl ether.
Further, the base is any one of potassium phosphate anhydrous, potassium carbonate, cesium fluoride, potassium fluoride, cesium carbonate, potassium phosphate trihydrate, potassium hydroxide, or sodium hydroxide.
Furthermore, the temperature of the coupling reaction is 80-160 ℃, and the reaction time is 12-48 h.
Furthermore, the temperature of the coupling reaction is 120-140 ℃, and the reaction time is 24-48 h.
Further, a transition metal catalyst, a ligand and an aromatic C-NO2The molar ratio of (1) - (10) to (5-100); aromatic C-NO2The mol ratio of the organic silicon reagent to the alkali is 1 (1-5) to 1-10.
(III) advantageous effects
The invention provides a transition metal catalyzed aromatic C-NO2The Hiyama coupling method is to use aromatic C-NO in an organic solvent under the protection of nitrogen2And an organic silicon reagent is taken as a substrate, cross coupling reaction is carried out under the action of alkali through the action of a transition metal catalyst and a ligand, and the aromatic compound is obtained through a column chromatography or recrystallization method. The method has the advantages of low synthesis operation difficulty, simple post-treatment, high conversion rate, good substrate universality and the like, can construct a series of aromatic compounds, and has application prospects in the fields of medicines, chemical industry and materials.
The main advantages of the invention are:
1. the invention firstly provides aromatic C-NO catalyzed by transition metal2Cross-coupling reaction with organosilicon reagents;
2. the coupling reaction raw materials involved in the invention have wide sources, high yield, low cost and good substrate stability and universality.
3. The method can be used for synthesizing a series of polyarylates and has wide application prospect in the fields of medicines, pesticides, photoelectric materials and the like.
Detailed Description
In order to make the objects, contents and advantages of the present invention clearer, the following detailed description of the embodiments of the present invention will be given in conjunction with examples.
This example presents a transition metal catalyzed aromatic C-NO2The Hiyama coupling method of (1), the method comprising: under the protection of nitrogen, 0.5mmol of nitroaromatic, 0.6mmol of organosilicon reagent and 0.05mmol of Pd (acac) are added20.1mmol RuPhos, 0.6mmol sodium hydroxide, evacuated and charged with nitrogen three times. 3mL of dioxane or ethylene glycol was added using a syringe and the reaction was carried out for 24h with an oil bath heated to 140 ℃. Cooling to room temperature, monitoring by TLC, adding water and a small amount of acetic acid, extracting by diethyl ether, removing the solvent by rotation, and separating by column chromatography to obtain the corresponding coupled product.
Example 1
The coupling product is:
white solid, yield 93%.1H NMR(500MHz,Chloroform)7.75(d,J＝7.5Hz,2H),7.58–7.46(m,4H),7.41–7.38(m,1H),6.98(d,J＝7.5Hz,2H),3.79(s,3H)。
Example 2
The coupling product is:
white solid, yield 95%.1H NMR (500MHz, Chloroform) 8.10-7.95 (m,2H), 7.85-7.66 (m,4H), 7.61-7.20 (m,3H),4.30(q, J ═ 11.8Hz,2H),1.30(t, J ═ 11.8Hz,3H)2(PCy3)2The product yield is 83%, and the effect is slightly worse than that of palladium by adopting a nickel catalyst.
White solid, yield 75%.
Example 3
The coupling product is:
white solid, yield 85%.1H NMR(500MHz,Chloroform)7.75(d,J＝7.5Hz,2H),7.58–7.46(m,4H),7.41–7.38(m,1H),6.98(d,J＝7.5Hz,2H),3.79(s,3H)。
Example 4
The coupling product is:
light yellowColor solid, yield 86%.1H NMR(500MHz,Chloroform)7.84–7.69(m,2H),7.59–7.35(m,5H),7.22–7.03(m,2H)。
Example 5
The coupling product is:
white solid, yield 87%.1H NMR(500MHz,Chloroform)7.80–7.65(m,4H),7.55–7.35(m,5H)。
Example 6
The coupling product is:
white solid, yield 94%.1H NMR(500MHz,Chloroform)8.95(dd,J＝7.4,1.5Hz,1H),8.50(dd,J＝6.0,2.9Hz,1H),7.89(d,J＝7.4Hz,1H),7.78(ddd,J＝6.7,4.2,2.1Hz,4H),7.46(t,J＝7.1Hz,2H),7.44–7.37(m,2H),7.34(td,J＝7.5,1.5Hz,1H)。
Example 7
The coupling product is:
pale yellow liquid, yield 80%.1H NMR(500MHz,Chloroform)7.89–7.77(m,2H),7.70(dd,J＝15.0,3.1Hz,1H),7.54–7.44(m,3H),7.44–7.35(m,1H),7.13(t,J＝14.9Hz,1H)。
Example 8
The coupling product is:
pale yellow liquid, yield 79%.1H NMR(500MHz,Chloroform)7.70(dd,J＝7.5,1.4Hz,1H),7.64(d,J＝7.5Hz,2H),7.40(dd,J＝7.5,1.4Hz,1H),7.13(t,J＝7.5Hz,1H),7.05(d,J＝7.5Hz,2H),3.79(s,3H)。
Example 9
The coupling product is:
pale yellow liquid, yield 75%.1H NMR(500MHz,Chloroform)7.93–7.75(m,2H),7.60-7.58(m,1H),7.53–7.24(m,10H),2.34(s,3H)。
Example 10
The coupling product is:
white solid, yield 72%.1H NMR(500MHz,Chloroform)7.79–7.59(m,2H),7.58–7.41(m,4H),7.07–6.93(m,2H),3.79(s,3H)。
The above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. Aromatic C-NO catalyzed by transition metal2The Hiyama coupling method of (a), wherein the coupling method comprises: in an organic solvent under nitrogen atmosphere, using aromatic C-NO2And an organic silicon reagent as a substrate, performing cross coupling reaction under the action of alkali through the action of a transition metal catalyst and a ligand, and obtaining an aromatic compound through methods such as column chromatography or recrystallization; the aromatic C-NO2The structural formula of (A) is: Ar-NO2(I) Wherein Ar is phenyl, substituted phenyl, naphthyl, heteroaryl or substituted heteroaryl; the structural formula of the organic silicon reagent is as follows: R-SiX3(II), wherein R is phenyl, substituted phenyl, heteroaryl or substituted heteroaryl, and X is fluorine, methyl, methoxy or ethoxy; the cross-coupling reaction equation is as follows:
2. the coupling process of claim 1, wherein in formula (I), the substituted phenyl group is an alkyl, alkoxy, morphinyl, ester, nitro, fluoro, trifluoromethyl substituted phenyl group; the aromatic hetero group is a nitrogen-containing aromatic hetero group; in the formula (II), the substituted phenyl is alkyl, alkoxy, trifluoromethyl, ester group, dimethylamino and cyano-substituted phenyl.
3. The coupling process of claim 2, wherein the nitrogen-containing heteroaryl group is a pyridine, quinoline, isoquinoline, or indole heteroaryl group.
4. The coupling process of claim 1, wherein the transition metal catalyst is Pd (acac)2、Pd(OAc)2、PdCl2、Pd(CH3CN)2Cl2、Pd(PPh3)2Cl2、Pd(dppf)Cl2、Pd2(dba)3、Pd(TFA)2、Pd2(allyl)2Cl2、Ni(COD)2、NiCl2(PCy3)2Any one of them.
5. The coupling method of claim 1, wherein the ligand is BrettPhos, SPhos, IPr, IMes, SIMes, XPhos, RuPhos, PtBu3Any one of DPPF and BINAP.
6. The coupling process of claim 1, wherein the organic solvent is any one of dioxane, toluene, tetrahydrofuran, N-dimethylformamide, isopropanol, ethanol, ethylene glycol, or ethylene glycol dimethyl ether.
7. The coupling process of claim 1, wherein the base is any one of potassium phosphate anhydrous, potassium carbonate, cesium fluoride, potassium fluoride, cesium carbonate, potassium phosphate trihydrate, potassium hydroxide, or sodium hydroxide.
8. The coupling method according to claim 1, wherein the temperature of the coupling reaction is 80 to 160 ℃ and the reaction time is 12 to 48 hours.
9. The coupling method according to claim 7, wherein the temperature of the coupling reaction is 120 to 140 ℃ and the reaction time is 24 to 48 hours.
10. The coupling process of claim 1, wherein the transition metal catalyst, ligand and aromatic C-NO2The molar ratio of (1) - (10) to (5-100); the aromatic C-NO2The mol ratio of the organic silicon reagent to the alkali is 1 (1-5) to 1-10.
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Citations (5)
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|---|---|---|---|---|
| US20020183516A1 (en) * | 2000-06-06 | 2002-12-05 | Denmark Scott E. | Cross-coupling reaction of organosilicon nucleophiles |
| CN103172479A (en) * | 2013-03-25 | 2013-06-26 | 绍兴文理学院 | Preparation method for biaryl through palladium catalysis |
| JP2018070527A (en) * | 2016-10-31 | 2018-05-10 | 東ソー株式会社 | Method for producing aromatic amine |
| JP2018076288A (en) * | 2016-10-31 | 2018-05-17 | 東ソー株式会社 | Method for producing aromatic compound |
| CN108610225A (en) * | 2018-03-12 | 2018-10-02 | 湖南科技大学 | A kind of method that transition metal-catalyzed nitro-aromatic prepares fragrant alkynes with terminal aryl group alkynes cross-coupling |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20020183516A1 (en) * | 2000-06-06 | 2002-12-05 | Denmark Scott E. | Cross-coupling reaction of organosilicon nucleophiles |
| CN103172479A (en) * | 2013-03-25 | 2013-06-26 | 绍兴文理学院 | Preparation method for biaryl through palladium catalysis |
| JP2018070527A (en) * | 2016-10-31 | 2018-05-10 | 東ソー株式会社 | Method for producing aromatic amine |
| JP2018076288A (en) * | 2016-10-31 | 2018-05-17 | 東ソー株式会社 | Method for producing aromatic compound |
| CN108610225A (en) * | 2018-03-12 | 2018-10-02 | 湖南科技大学 | A kind of method that transition metal-catalyzed nitro-aromatic prepares fragrant alkynes with terminal aryl group alkynes cross-coupling |
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