CN104497018B - Triazole-copper perchlorate complex with p-fluorophenylboronic acid catalyzing effect and preparation method of triazole-copper perchlorate complex - Google Patents

Triazole-copper perchlorate complex with p-fluorophenylboronic acid catalyzing effect and preparation method of triazole-copper perchlorate complex Download PDF

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CN104497018B
CN104497018B CN201410767896.6A CN201410767896A CN104497018B CN 104497018 B CN104497018 B CN 104497018B CN 201410767896 A CN201410767896 A CN 201410767896A CN 104497018 B CN104497018 B CN 104497018B
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triazole
boric acid
clo
fluorobenzoic boric
complex
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CN104497018A (en
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王英
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Tianjin Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a preparation method of {[Cu(L)] (ClO4).0.25H2O} (1) (L=4-(3-(4H-1, 2, 4-triazole-4-yl)phenyl)-4H-1, 2, 4-triazole). The complex is prepared by using a hydrothermal method comprising the step of reacting Cu(ClO4)2 and L under a 100-DEG C hydrothermal condition. The invention further discloses application of a copper complex, namely {[Cu(L)] (ClO4).0.25H2O} (1) (L=4-(3-(4H-1, 2, 4-triazole-4-yl)phenyl)-4H-1, 2, 4-triazole) as a catalyst for coupled reaction of p-fluorophenylboronic acid.

Description

Have and be catalyzed triazole-cupric perchlorate coordination compound to fluorobenzoic boric acid and preparation method thereof
The present invention obtains state natural sciences fund general project (21471113), Tianjin Municipal Education Commission funded projects (20140506), Tianjin Normal University's Middl-age and youth faculty Academic innovations propulsion planning item and Tianjin innovation team of institution of higher education Training plan subsidizes (TD12-5038).
Technical field
The invention belongs to Inorganic synthese technical field, it is related to copper complex { [Cu (L)] (ClO4)·0.25H2O} (1) (L =4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole) preparation method and as to fluorobenzoic boric acid be coupled The application of the catalyst aspect of reaction.
Background technology
One active field is always with the research that transition metal complex catalysis carries out high selectivity.With common Synthesizing mean is difficult to the reaction realized, and busy use transition metal complex can a step complete in a mild condition.Therefore, adopt Make catalyst of metal complex and develop the organic synthesis of high selectivity, high conversion, be very interesting Problem.In organic synthesiss, typically conventional transition metal has nickel, palladium, copper, ruthenium, rhodium, manganese etc., and wherein palladium complex show many Sample catalysiss.Palladium catalysed cross coupling reaction species is a lot, and these reactions are in synthesis of natural product, polymer, functional material, liquid All have been widely used in crystalline substance, drug molecule and bioactive compound.But palladium catalyst is relatively costly, if can be with cheap Copper complex replaces expensive palladium catalyst, realizes the process of reaction, not only can be cost-effective, and is expected to industrial metaplasia Produce.
1,2,4- triazole and its derivant have the coordination feature of pyrazoles and imidazoles concurrently, are that the stronger bridging of coordination ability is joined Body, has synthesized and has characterized substantial amounts of monokaryon, multinuclear and multidimensional compound at present.These parts can be former with the nitrogen on 1,2 Son and metallic ion coordination form N1, N2- bridging pattern, and for 4 unsubstituted 1,2,4- triazole derivatives can pass through 2,4 On nitrogen-atoms formed N2, N4- bridging pattern, this N2, N4- bridging pattern is with the N1 of imidazoles in metalloenzyme, N3- bridging pattern Similar.Specific use for triazole class compounds is also manifested by the design of molecular device, and synthesis has different dimensions Metal complex is to complete the vital step of device.
The present invention is from Cu (ClO4)2With 4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole (L) 100oC hydrothermal condition gets off to prepare copper complex { [Cu (L)] (ClO4)·0.25H2O} (1).Catalysis experiments prove, This coordination compound can be applied as to the catalyst of fluorobenzoic boric acid coupling reaction.
Content of the invention
Further object is that providing a kind of isophthalic double triazole copper complex { [Cu (L)] (ClO4)· 0.25H2O } (1) monocrystalline and preparation method thereof.
For this current inventor provides following technical scheme：
Double triazole copper complex { [Cu (L)] (ClO of isophthalic4)·0.25H2O } (1) (L=4- (3- (4H-1,2,4- tri- Azoles -4- base) phenyl) -4H-1,2,4- triazole) and structural motif as shown in Figure 1；L=4- (3- (4H-1,2,4- triazole-4-yl) Phenyl) -4H-1,2,4- triazole；
The present invention further discloses double triazole copper complex { [Cu (L)] (ClO of isophthalic4)·0.25H2O} (1) (L = 4- (3- (4H-1,2,4- triazole-4-yls) phenyl) -4H-1,2,4- triazoles) monocrystalline is it is characterised in that this mono-crystalline structures adopts APEX II CCD single crystal diffractometer, using through graphite monochromatised Mok alpha ray (λ=0.71073) be incident radiation, Withω-2θScan mode collects point diffraction, obtains cell parameter through least square refinement, from difference Fourier electron density Desire to make money or profit and solve single crystal data with software：
The crystallographic data of table 1. coordination compound 1
Double triazole copper complex { [Cu (L)] (ClO of isophthalic of the present invention4)·0.25H2O} (1) (L = 4-(3- (4H-1,2,4- triazole-4-yls) phenyl) -4H-1,2,4- triazoles) monocrystalline preparation method, its feature adopt " hydro-thermal method ", In CH3CN and H2In O, by Cu (ClO4)2With L ligand 1 00oReact under C hydrothermal condition, obtain being suitable for X-ray single crystal diffraction Yellow rhabdolith.Wherein CH3CN and H2The volume ratio of O is 4:6, Cu (ClO4)2Mol ratio with L is 1:1；
The more detailed preparation method of the present invention is as follows：
A kind of double triazole copper complex { [Cu (L)] (ClO of isophthalic4)·0.25H2O} (1) (L = 4-(3-(4H-1,2, 4- triazole-4-yl) phenyl) -4H-1,2,4- triazoles) monocrystalline preparation method, its feature adopt " hydro-thermal method ", in CH3CN and H2In O, by Cu (ClO4)2With L ligand 1 00oReact under C hydrothermal condition, the yellow obtaining being suitable for X-ray single crystal diffraction is bar-shaped Crystal.Wherein CH3CN and H2The volume ratio of O is 4:6, Cu (ClO4)2Mol ratio with L is 1:1；
Solvent of the present invention is mixed solvent, CH3CN and H2O.
Wherein Cu (ClO4)2Mol ratio with L is 1:1.
The present invention further discloses copper complex { [Cu (L)] (ClO4)·0.25H2O} (1) (L = 4-(3-(4H- 1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole) as the application to fluorobenzoic boric acid coupling reaction catalyst aspect.
A kind of double triazole copper complex { [Cu (L)] (ClO of isophthalic disclosed by the invention4)·0.25H2O}(1) (L = 4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole) monocrystalline had the advantage that to be with feature：
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) { [Cu (L)] (ClO prepared by the present invention4)·0.25H2O}n(1) (L=4- (3- (4H-1,2,4- tri- Azoles -4- base) phenyl) -4H-1,2,4- triazoles) low production cost, method simplicity, suitable large-scale production.
Brief description
Fig. 1：The crystal structure primitive figure of coordination compound 1；
Fig. 2：The tomograph of coordination compound 1；
Fig. 3：The nuclear-magnetism figure of 4,4'- DfBP.
Specific embodiment
With reference to embodiment, the present invention is described further, and embodiment is only explanatory, is in no way intended to it Limit the scope of the present invention by any way.All of raw material is all to be bought from chemical reagents corporation both domestic and external, does not have Use through continuation purification but directly.Raw materials used by commercially available.
Embodiment 1
The preparation of 4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole (L) part
It is separately added into m-diaminobenzene. (1 in the 50 mL three neck round bottom flasks equipped with magneton, reflux condenser and thermometer Mmol), double formylhydrazines (2 mmol), start stirring at 100 DEG C, react 12 hours.After reaction terminates, reactant liquor is down to room Temperature, separates out a large amount of precipitation, by precipitation water and ethyl alcohol recrystallization, yield 86%.Elementary analysiss C10H8N6Theoretical value：C, 56.60； H, 3.80；N, 39.60.Experiment value：C, 56.56；H, 3.75；N, 39.56.M-diaminobenzene., the mol ratio of double formylhydrazines is 1:2.
Embodiment 2
Cu(ClO4)2With 4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole) mol ratio of (L) is 1:1；
L (0.0424 g, 0.2 mmol), Cu (ClO4)2(0.0691 g, 0.2 mmol), H2O (6 mL), CH3CN (4 mL), hydro-thermal 100oC was slowly dropped to room temperature after tri- days.There is the yellow of suitable X-ray single crystal diffraction analysis bar-shaped after driving kettle Crystal.Yield：35% (being calculated based on L).Elementary analysiss (C10H8.5ClCuN6O4.25) theoretical value (%)：C, 30.67；H, 2.03； N, 19.51.Measured value：C, 30.63；H, 2.06；N, 19.59.We also attempted other ratios, such as Cu (ClO4)2With L's Mol ratio is 2:1, then the length of no matter the hydro-thermal reaction time, all cannot get crystalline compound.Therefore Cu (ClO4)2With L mole Than for 1:1 is optimum response proportioning.
Embodiment 3
Crystal structure determination adopts APEX II CCD single crystal diffractometer, using through graphite monochromatised Mok alpha ray (λ =0.71073) it is incident radiation, withω-2θScan mode collects point diffraction, obtains structure cell ginseng through least square refinement Number, solves crystal structure from difference Fourier electron density map using software, and through Lorentz lorentz and polarity effect correction.All of H atom is synthesized and determined through preferable position calculation by difference Fourier.Detailed axonometry data is shown in Table 1.Structural motif is shown in Fig. 1, the three dimensional structure of coordination compound is shown in Fig. 2.
The crystallographic data of table 1 coordination compound 1
Embodiment 4
One active field is always with the research that transition metal complex catalysis carries out high selectivity.With common Synthesizing mean is difficult to the reaction realized, and busy use transition metal complex can a step complete in a mild condition.Therefore, adopt Make catalyst of metal complex and develop the organic synthesis of high selectivity, high conversion, be very interesting Problem.In organic synthesiss, typically conventional transition metal has nickel, palladium, copper, ruthenium, rhodium, manganese etc., and wherein palladium complex show many Sample catalysiss.Palladium catalysed cross coupling reaction species is a lot, and these reactions are in synthesis of natural product, polymer, functional material, liquid All have been widely used in crystalline substance, drug molecule and bioactive compound.But palladium catalyst is relatively costly, if can be with cheap Copper complex replaces expensive palladium catalyst, realizes the process of reaction, not only can be cost-effective, and is expected to industrial metaplasia Produce.
1,2,4- triazole and its derivant have the coordination feature of pyrazoles and imidazoles concurrently, are that the stronger bridging of coordination ability is joined Body, has synthesized and has characterized substantial amounts of monokaryon, multinuclear and multidimensional compound at present.These parts can be former with the nitrogen on 1,2 Son and metallic ion coordination form N1, N2- bridging pattern, and for 4 unsubstituted 1,2,4- triazole derivatives can pass through 2,4 On nitrogen-atoms formed N2, N4- bridging pattern, this N2, N4- bridging pattern is with the N1 of imidazoles in metalloenzyme, N3- bridging pattern Similar.Specific use for triazole class compounds is also manifested by the design of molecular device, and synthesis has different dimensions Metal complex is to complete the vital step of device.
The present invention is from Cu (ClO4)2With 4- (3- (4H-1,2,4- triazole-4-yl) phenyl) -4H-1,2,4- triazole (L) 100oC hydrothermal condition gets off to prepare copper complex { [Cu (L)] (ClO4)·0.25H2O} (1).Catalysis experiments prove, This coordination compound can be applied as to the catalyst of fluorobenzoic boric acid coupling reaction
Weigh 1 g to fluorobenzoic boric acid in 25 mL beakers, 0.2 g Cs2CO3, (the cooperation of 3 mL DMF and 0.1 g catalyst Thing 1), stir 1 hour under room temperature, TLC monitors (PE:EA = 1:1) react completely, 10 mLCH2Cl2Again with 20 after extracted products ML distilled water wash, organic faciess sewage MgSO4It is dried, filter, precipitation, the crude product obtaining strips post with petroleum ether, obtains To 4,4'- DfBP.

Claims (2)

1. application in terms of as the catalyst to fluorobenzoic boric acid coupling reaction for the double triazole copper complex monocrystalline of isophthalic, its feature It is that this mono-crystalline structures adopts APEX II CCD single crystal diffractometer, using through graphite monochromatised Mok alpha ray, λ= 0.71073 is incident radiation, withω-2θScan mode collects point diffraction, obtains cell parameter through least square refinement, Solve single crystal data from difference Fourier electron density map using software：
[Cu (L)] (ClO of the double triazole copper complex mono-crystalline structures of isophthalic4)·0.25H2O, L=4- (3- (4H-1,2,4- tri- Azoles -4- base) phenyl) -4H-1,2,4- triazole.
2. the application described in claim 1, wherein adopts the method to fluorobenzoic boric acid coupling reaction as follows：
To fluorobenzoic boric acid 4,4'- DfBP
Weigh 1 g to fluorobenzoic boric acid in 25 mL beakers, 0.2 g Cs2CO3, 3 mL DMF and 0.1 g catalyst complexes list Crystalline substance, stirs 1 hour under room temperature, and TLC monitoring reaction is complete, 10 mLCH2Cl2Again with 20 mL distilled water washs after extracted products, have The anhydrous MgSO of machine phase4It is dried, filter, precipitation, the crude product obtaining strips post with petroleum ether, obtains 4,4'- DfBP.
CN201410767896.6A 2014-12-15 2014-12-15 Triazole-copper perchlorate complex with p-fluorophenylboronic acid catalyzing effect and preparation method of triazole-copper perchlorate complex Expired - Fee Related CN104497018B (en)

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