CN111440052B - Stille coupling method for aromatic nitro compound catalyzed by transition metal - Google Patents
Stille coupling method for aromatic nitro compound catalyzed by transition metal Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- 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
- C07C1/325—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 metal atom
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- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
Abstract
The invention provides a Stille coupling method for an aromatic nitro compound catalyzed by transition metal, which comprises the steps of taking the aromatic nitro compound and an organic tin compound as substrates in an organic solvent under the protection of nitrogen, carrying out cross coupling reaction under the action of alkali through the action of a transition metal catalyst and a ligand, and obtaining the aromatic compound through a column chromatography or recrystallization method. The method has the advantages of simple operation, low price, high product conversion rate and good substrate applicability; can be used for synthesizing a series of aromatic compounds, and the compounds have wide application value in the fields of pesticides, medicines, materials and the like.
Description
Technical Field
The invention belongs to the technical field of organic catalytic synthesis, and particularly relates to a Stille coupling method for catalyzing aromatic nitro compounds by transition metals.
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. In addition, 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. A transition metal catalyzes a Suzuki cross-coupling reaction of an aryl nitro compound [ angelw.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; chi.j.org.chem., 2016,36,1021; RSC adv.,2016,6,33380; eur.j.org.chem.,2017,3244; total. Commun.,2017,94,33; j.am.chem.soc.,2017,139,9423; related documents report that C-O, C-S, C-C and C-N bonds are constructed by Angew. Chem., int.Ed.,2017,56,13307. Therefore, it is very important to develop a transition metal catalyzed aryl nitro compound to perform cross-coupling reaction with other nucleophilic reagents.
Disclosure of Invention
Technical problem to be solved
The invention provides a Stille coupling method of a transition metal catalyzed aromatic nitro compound, which aims to solve the technical problem of how to realize cross coupling reaction of the transition metal catalyzed aromatic nitro compound and other nucleophilic reagents.
(II) technical scheme
In order to solve the technical problems, the invention provides a Stille coupling method of a transition metal catalytic aromatic nitro compound, which comprises the steps of taking an aromatic nitro compound and an organic tin compound as substrates in an organic solvent under the protection of nitrogen, carrying out cross coupling reaction under the action of alkali through the action of a transition metal catalyst and a ligand, and obtaining the aromatic compound through a column chromatography or recrystallization method; wherein the structural formula of the aromatic nitro compound is Ar-NO 2 Wherein Ar is phenyl, substituted phenyl, naphthyl, heteroaryl or substituted heteroaryl; the structural formula of the organic tin compound is R-SnBu 3 Wherein R is phenyl, substituted phenyl, heteroaryl or substituted heteroaryl.
Further, the transition metal catalyst is Pd (acac) 2 、Pd(OAc) 2 、PdCl 2 、Pd(PPh 3 ) 2 Cl 2 、Pd(dppf)Cl 2 、Pd 2 (dba) 3 、Pd(TFA) 2 、Pd 2 (allyl) 2 Cl 2 、Ni(COD) 2 、NiCl 2 (PCy 3 ) 2 Any one of them.
Further, the ligand is Brettphos, SPhos, IPr, IMes, SIMes, XPhos, or,RuPhos、PtBu 3 Any one of DPPF and BINAP.
Further, the organic solvent is any one of dioxane, toluene, tetrahydrofuran, N-dimethylformamide, acetonitrile, methyl tert-butyl ether, N-heptane, isopropanol or ethylene glycol dimethyl ether.
Further, the base is any one of potassium phosphate trihydrate, anhydrous potassium phosphate, potassium carbonate, cesium fluoride, cesium carbonate, potassium acetate, dipotassium hydrogen phosphate, potassium hydroxide, or triethylamine.
Furthermore, the temperature of the coupling reaction is 80-160 ℃, the reaction time is 12-48 h, the molar ratio of the transition metal catalyst, the ligand and the aromatic nitro compound is 1 (1-10) to (5-100), and the molar ratio of the aromatic nitro compound, the organic tin compound and the alkali is 1 (1-5) to (1-10).
Furthermore, the temperature of the coupling reaction is 120-140 ℃, and the reaction time is 24-48 h.
Furthermore, an additive is added in the coupling reaction.
Further, the additive is tetrabutylammonium bromide, tris (3,6-dioxaheptyl) amine or 18-crown-6.
Furthermore, the molar ratio of the additive to the aromatic nitro compound is (0.1-1): 5.
(III) advantageous effects
The invention provides a Stille coupling method for an aromatic nitro compound catalyzed by transition metal, which comprises the steps of taking the aromatic nitro compound and an organic tin compound as substrates in an organic solvent under the protection of nitrogen, carrying out cross coupling reaction under the action of alkali through the action of a transition metal catalyst and a ligand, and obtaining the aromatic compound through a column chromatography or recrystallization method. The method has the advantages of simple operation, low price, high product conversion rate and good substrate applicability; can be used for synthesizing a series of aromatic compounds, and the compounds have wide application value in the fields of pesticides, medicines, materials and the like.
The beneficial effects of the invention specifically comprise:
1. the invention firstly proposes the cross coupling reaction of the aryl nitro compound and the organic tin compound catalyzed by the transition metal;
2. the coupling reaction involved in the invention has the advantages of simple operation, simple and easily obtained raw material source, high yield and good substrate universality;
3. the invention can be used for synthesizing a series of aromatic compounds, and the synthesized compounds have wide application prospects 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.
The invention provides a Stille coupling method for catalyzing aromatic nitro compounds by transition metals, which has the following reaction equation:
wherein the structural formula of the aromatic nitro compound is Ar-NO 2 Ar is phenyl, substituted phenyl, naphthyl, heteroaryl or substituted heteroaryl; the structural formula of the organotin compound is R-SnBu 3 And R is phenyl, substituted phenyl, heteroaryl or substituted heteroaryl.
The choice of catalyst and ligand has an effect on the yield of the product, and this example mainly describes the specific operation of the palladium and phosphorus ligands, but the invention is not limited to this type of catalytic system.
The specific operation steps are as follows: adding 0.5mmol of aromatic nitro compound, 0.6mmol of organotin compound, 5% mmol of Pd (acac) under nitrogen protection 2 10 mmol of XPhos,0.6mmol of potassium phosphate trihydrate and 0.01mmol of 18-crown-6, and evacuation and nitrogen purging were carried out three times. 10mL of dioxane or toluene 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 with diethyl ether, removing the solvent by rotation, and separating by column chromatography to obtain the corresponding coupling product.
Example 1
White solid, yield 80%. 1 H NMR(500MHz,Chloroform)δ7.75(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
White solid, yield 85%. 1 H NMR (500mhz, chloroform) δ 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). Using NiCl 2 (PCy 3 ) 2 The product yield is 75%, and the effect is slightly worse than that of palladium when a nickel catalyst is adopted.
White solid, yield 68%.
Example 3
White solid, yield 63%. 1 H NMR(500MHz,Chloroform)δ7.75(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
Pale yellow solid, yield 78%. 1 H NMR(500MHz,Chloroform)δ7.84–7.69(m,2H),7.59–7.35(m,5H),7.22–7.03(m,2H)。
Example 5
White solid, yield 84%. 1 H NMR(500MHz,Chloroform)δ7.80–7.65(m,4H),7.55–7.35(m,5H)。
Example 6
White solid, yield 86%. 1 H NMR(500MHz,Chloroform)δ8.95(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
Pale yellow liquid, yield 83%. 1 H NMR(500MHz,Chloroform)δ7.89–7.77(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
Pale yellow liquid, yield 78%. 1 H NMR(500MHz,Chloroform)δ7.70(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
Pale yellow liquid, yield 78%. 1 H NMR(500MHz,Chloroform)δ7.93–7.75(m,2H),7.60-7.58(m,1H),7.53–7.24(m,10H),2.34(s,3H)。
Example 10
White solid, yield 80%. 1 H NMR(500MHz,Chloroform)δ7.79–7.59(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 (4)
1. A Stille coupling method of aromatic nitro compounds catalyzed by transition metals is characterized by comprising the steps of taking the aromatic nitro compounds and organic tin compounds as substrates in an organic solvent under the protection of nitrogen, carrying out cross coupling reaction under the action of alkali through the action of transition metal catalysts, ligands and additives, and obtaining aromatic compounds through a column chromatography or recrystallization method; the reaction equation is as follows:
wherein the structural formula of the aromatic nitro compound is Ar-NO 2 Wherein Ar is phenyl, substituted phenyl, naphthyl, heteroaryl or substituted heteroaryl;
the structural formula of the organic tin compound is R-SnBu 3 Wherein R is phenyl, substituted phenyl, heteroaryl or substituted heteroaryl;
the transition metal catalyst is Pd (acac) 2 、Pd(OAc) 2 、PdCl 2 、Pd(PPh 3 ) 2 Cl 2 、Pd(dppf)Cl 2 、Pd 2 (dba) 3 、Pd(TFA) 2 、Pd 2 (allyl) 2 Cl 2 、Ni(COD) 2 、NiCl 2 (PCy 3 ) 2 Any one of the above; the ligand is Brettphos, SPhos, IPr, IMes, SIMes, XPhos, ruPhos, ptBu 3 Any one of DPPF and BINAP;
the organic solvent is any one of dioxane, toluene, tetrahydrofuran, N-dimethylformamide, acetonitrile, methyl tert-butyl ether, N-heptane, isopropanol or ethylene glycol dimethyl ether;
the alkali is any one of potassium phosphate trihydrate, anhydrous potassium phosphate, potassium carbonate, cesium fluoride, cesium carbonate, potassium acetate, dipotassium hydrogen phosphate, potassium hydroxide or triethylamine;
the additive is tetrabutylammonium bromide, tris (3,6-dioxaheptyl) amine or 18-crown-6.
2. A Stille coupling method according to claim 1, wherein the temperature of the coupling reaction is 80-160 ℃, the reaction time is 12-48 h, the molar ratio of the transition metal catalyst, the ligand and the aromatic nitro compound is 1 (1-10) to (5-100), and the molar ratio of the aromatic nitro compound, the organic tin compound and the base is 1 (1-5) to (1-10).
3. A Stille coupling method according to claim 2, wherein the temperature of the coupling reaction is 120 to 140 ℃ and the reaction time is 24 to 48 hours.
4. A Stille coupling process according to claim 1, wherein the molar ratio of additive to aromatic nitro compound is (0.1-1): 5.
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| JP7023080B2 (en) * | 2016-10-31 | 2022-02-21 | 東ソー株式会社 | Method for producing aromatic compounds |
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