CN105906670A - Fluorenone nickel pyridine nano-cluster and method for preparing same - Google Patents
Fluorenone nickel pyridine nano-cluster and method for preparing same Download PDFInfo
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- CN105906670A CN105906670A CN201610280894.3A CN201610280894A CN105906670A CN 105906670 A CN105906670 A CN 105906670A CN 201610280894 A CN201610280894 A CN 201610280894A CN 105906670 A CN105906670 A CN 105906670A
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
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- 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
- B01J31/22—Organic complexes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/88—Growth and elimination reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- 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
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
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- 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
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
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- 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
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4266—Sonogashira-type, i.e. RY + HC-CR' triple bonds, in which R=aryl, alkenyl, alkyl and R'=H, alkyl or aryl
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
Abstract
The invention discloses a fluorenone nickel pyridine nano-cluster and a method for preparing the same. The fluorenone nickel pyridine nano-cluster and the method have the advantages that fluorenone pyridine organic ligand solution is added into metal salt solution drop by drop, reaction products are ultrasonically dispersed after reaction is completely carried out, are centrifugally separated from one another, are washed and are dried under vacuum conditions to obtain the ligand-metal nano-cluster, procedures for preparing the fluorenone nickel pyridine nano-cluster are simple, and the fluorenone nickel pyridine nano-cluster is low in cost; solvents, the concentration of reactants, the reaction time and the temperatures can be changed, and accordingly the morphology of the fluorenone nickel pyridine nano-cluster can be effectively regulated and controlled; C-C cross coupling reaction can be efficiently catalyzed by the fluorenone nickel pyridine nano-cluster prepared by the aid of the method, the yield can reach 70% at least, and accordingly the fluorenone nickel pyridine nano-cluster can be widely applied to the field of catalysis.
Description
Technical field
The invention belongs to metal organic nanocomposite field, be specifically related to a kind of for being catalyzed carbon-carbon cross coupling reaction
Fluorenone pyridine nickel nano-cluster and preparation method thereof.
Background technology
Carbon-carbon cross coupling reaction is one of most important means in organic synthesis, is also that synthesis biaryl compound has most
The study hotspot in the fields such as one of method of effect, always catalytic chemistry, organic chemistry and materials chemistry.Traditional catalyst
Mainly Pd (PPh3)4Etc. palladium metal organic catalyst, the catalysis activity of this kind of catalyst is high, and substrate range of choice is wide, but its
Be prone in aromatic hydrocarbons generation aryl exchange reaction, course of reaction to be easily formed palladium black, building-up process is complicated, difficulty is big, expensive,
Phosphine ligands, to air and moisture-sensitive, needs the effective catalytic reaction of ability in inert gas atmosphere, pollution environment etc. many
Deficiency, therefore, for finding new and effective cheap catalyst, researchers' unremitting effort always.
In recent years, develop new and effective non-Phosphine ligands or the catalyst system and catalyzing without part is more paid close attention to by people, and achieved with
Certain progress, as P é rez-Lorenzo report a kind of palladium nanoparticle catalyst (J.Phys.Chem.Lett.2012,3,
167) and the disclosed a kind of spiral shell fluorenes pyridine palladium nano-particles of Zhao Xiuhua et al. and preparation method thereof (CN103951611A,
2014.7.30 disclose), these catalyst activity are good, and preparation process is relatively easy, but still select expensive Metal Palladium,
Relatively costly and stability is not good enough；The present invention select low-cost metallic nickel replace precious metal palladium to be prepared for a kind of nanometer multiple
Condensation material, the atomic radius of nickel is less than palladium metal radius, and nucleophilie nucleus ability is strong, the electronegativity of substrate is not so good as Pd sensitivity, has
Universal application.
Part select to the activation of metal with stably play vital effect.With it has been reported that or disclosed nickel catalysis material
(J.Am.Chem.Soc.2006,128,5361 compared by material；J.Am.Chem.Soc.2013,135,624；
CN104668577A, 2015.6.3 are open；CN104628628A, 2015.5.20 are open), the Fluorenone pyridine in the present invention
Pyridine ring, phenyl ring and the five-membered ring comprised in organic ligand defines conjugation delocalization big π key, has specific HOMO highest occupied molecular orbital
(HOMO) and lowest unoccupied molecular orbital (LUMO) energy level, in pyridine ring, nitrogen-atoms is easily coordinated with nickel ion, You Jipei
The conjugation delocalized electron of body produces specific effect to the valence electron d track of Ni (II), thus changes the catalysis activity of Ni (II)；This
Outward, there is C=O bond on 9 in Fluorenone pyridine ligand, the delocalization of part electronics also can be produced unique impact, make
When it is coordinated with nickel (II), the outer-shell electron Rotating fields on nickel ion produces impact, thus forms the nanometer with unique physico-chemical property
Composite.
Summary of the invention
The technical problem to be solved is, for the deficiencies in the prior art, it is provided that a kind of low price, preparation are simply
And the high Fluorenone pyridine nickel nano-cluster of catalytic efficiency and preparation method thereof.
The present invention solves that the technical scheme that above-mentioned technical problem is used is: the Fluorenone pyridine of a kind of efficient catalytic coupling reaction
The preparation method of nickel nano-cluster, comprises the following steps:
(1) Fluorenone pyridine organic ligands is dissolved in solvent it is configured to that Fluorenone pyridine that concentration is 10～20mmol/L is organic joins
Liquid solution, is labeled as solution A；
(2) nickel salt is dissolved in deionized water it is configured to the nickel salt aqueous solution that concentration is 5～10mmol/L, be labeled as B molten
Liquid；
(3) with vigorous stirring, solution A is slowly added dropwise to B solution (Fluorenone pyridine organic ligands and nickel ion
The ratio of the amount of material is 2～4:1), drip and be stirred vigorously complete follow-up continuing, and react 30～60min in 60～90 DEG C,
React mixture ultrasonic disperse 30min, centrifugation after terminating, discard supernatant liquid, be precipitated thing；
(4) by gained sediment respectively with deionized water and ethanol washing, ultrasonic disperse, centrifugation, upper solution is discarded
To remove free ion and the organic ligand not being coordinated, then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine
Nickel nano-cluster；
Preferably, described solvent is the one or any combination in propyl alcohol, isopropanol, ethanol；
Preferably, described nickel salt is one or more in nickel chloride, nickel acetate or nickel nitrate；
Preferably, entitled the 2 of described Fluorenone pyridine organic ligands, 7-bis-(4-pyridine)-9-Fluorenone, its molecular formula is
C23H14N2O。
Preferably, described Fluorenone pyridine nickel nano-cluster is as effective catalyst catalysis carbon-carbon cross coupling reaction.
The present invention also provides for a kind of Fluorenone pyridine nickel nano-cluster, and described Fluorenone pyridine nickel nano-cluster is according to above-mentioned Fluorenone pyridine nickel
The preparation method of nano-cluster prepares.
Compared with prior art, advantages of the present invention is as follows:
(1) electron delocalization of described Fluorenone pyridine organic ligands is strong, can be coordinated in two different directions with nickel ion, shape
Become Fluorenone pyridine nickel nano-cluster, this nanocluster material stable performance, it is possible to efficient catalytic coupling reaction, productivity be up to 70% with
On.
(2) there is C=O bond in described Fluorenone pyridine organic ligands, this also produces the shadow of uniqueness to the delocalization of part electronics
Ringing, when Fluorenone pyridine ligand is coordinated with nickel ion, delocalizedπelectron produces impact to the valence shell electron level structure of nickel ion,
So that the nickel nano-cluster formed has the physico-chemical property of uniqueness.
(3) present invention selects cheap nickel salt, reduces catalyst cost；And by controlling reaction time and temperature, it is achieved right
The regulation and control of Fluorenone pyridine nickel nano-cluster pattern so that it is there is good catalytic performance.
Accompanying drawing explanation
Fig. 1 is the scanning electron microscope (SEM) photograph of Fluorenone pyridine nickel nano-cluster of the present invention.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1
With vigorous stirring, the aqueous isopropanol (10mmol/L, 15mL) of Fluorenone pyridine is slowly dropped to nickel nitrate water-soluble
Liquid (5mmol/L, 15mL), continuing vigorous stirring is also reacted 60min at 60 DEG C, is reacted mixed system after terminating
Through ultrasonic disperse 30min, centrifugation, discard upper liquid, be precipitated thing；Gained sediment is used deionized water respectively
With ethanol washing, ultrasonic disperse, centrifugation, discard the ion that upper solution is dissociated and the organic ligand not being coordinated with removing,
Then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine nickel nano-cluster.With nano-cluster described in scanning electron microscopic observation
Pattern, as shown in Figure 1.
Embodiment 2
With vigorous stirring, the propanol solution (20mmol/L, 15mL) of Fluorenone pyridine is slowly dropped to nickel chloride aqueous solution
(5mmol/L, 15mL), continuing vigorous stirring is also reacted 30min at 90 DEG C, is reacted mixed system warp after terminating
Ultrasonic disperse 30min, centrifugation, discard upper liquid, be precipitated thing；By gained sediment respectively by deionized water and
Ethanol washing, ultrasonic disperse, centrifugation, discard the ion that upper solution is dissociated and the organic ligand not being coordinated with removing,
Then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine nickel nano-cluster.With nano-cluster described in scanning electron microscopic observation
Pattern.
Embodiment 3
With vigorous stirring, the ethanol solution (20mmol/L, 15mL) of Fluorenone pyridine is slowly dropped to nickel acetate aqueous solution
(10mmol/L, 15mL), continuing vigorous stirring is also reacted 60min at 90 DEG C, is reacted mixed system warp after terminating
Ultrasonic disperse 30min, centrifugation, discard upper liquid, be precipitated thing；By gained sediment respectively by deionized water and
Ethanol washing, ultrasonic disperse, centrifugation, discard the ion that upper solution is dissociated and the organic ligand not being coordinated with removing,
Then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine nickel nano-cluster.With nano-cluster described in scanning electron microscopic observation
Pattern.
Embodiment 4
With vigorous stirring, the ethanol solution (15mmol/L, 15mL) of Fluorenone pyridine is slowly dropped to nickel acetate aqueous solution
(6mmol/L, 15mL), continuing vigorous stirring is also reacted 50min at 80 DEG C, is reacted mixed system warp after terminating
Ultrasonic disperse 30min, centrifugation, discard upper liquid, be precipitated thing；By gained sediment respectively by deionized water and
Ethanol washing, ultrasonic disperse, centrifugation, discard the ion that upper solution is dissociated and the organic ligand not being coordinated with removing,
Then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine nickel nano-cluster.With nano-cluster described in scanning electron microscopic observation
Pattern.
With embodiment 1, embodiment 2, as a example by the Fluorenone pyridine nickel nano-cluster of embodiment 3 and embodiment 4 preparation, it is catalyzed
C-C cross-coupling reaction:
The Fluorenone pyridine nickel nano-cluster using above-described embodiment 1 preparation carries out catalytic reaction as catalyst, and reaction condition is:
By 1.0mmol 4-methoxybromobenzene, 1.2mmol phenyl boric acid and 3.0mmol KOH, in H in air atmosphere2O/EtOH
(3mL/4mL) reacting in mixed solvent, react 8h at 90 DEG C, productivity is 75%.Reaction equation is as follows:
The Fluorenone pyridine nickel nano-cluster using above-described embodiment 2 preparation carries out catalytic reaction as catalyst, and reaction condition is:
By 1.0mmol 4-iodobenzene ether, 1.2mmol styrene and 3.0mmol K2CO3, in H in air atmosphere2O/EtOH
(3mL/4mL) reacting in mixed solvent, react 6h at 80 DEG C, productivity is 96%.Reaction equation is as follows:
The Fluorenone pyridine nickel nano-cluster using above-described embodiment 3 preparation carries out catalytic reaction as catalyst, and reaction condition is:
By 1.0mmol 4-iodobenzene ether, 1.2mmol styrene and 2.0mmol Na2CO3, in N in air atmosphere, N-diformazan
Reaction in base formamide (DMF), reacts 15h at 140 DEG C, and productivity is 85%.Reaction equation is as follows:
The Fluorenone pyridine nickel nano-cluster using above-described embodiment 4 preparation carries out catalytic reaction as catalyst, and reaction condition is:
By 1.0mmol iodobenzene, 1.2mmol phenylacetylene and 3.0mmol NaOH, in H in air atmosphere2O/EtOH(1mL
/ 6mL) mixed solvent reacts, at 80 DEG C, react 4h, productivity is 80%.Reaction equation is as follows:
Claims (3)
1. the preparation method of a Fluorenone pyridine nickel nano-cluster, it is characterised in that described preparation method comprises the following steps:
Fluorenone pyridine organic ligands is dissolved in solvent that to be configured to the Fluorenone pyridine organic ligands that concentration is 10～20mmol/L molten
Liquid, is labeled as solution A；
Nickel salt is dissolved in deionized water and is configured to the nickel salt aqueous solution that concentration is 5～10mmol/L, be labeled as B solution；
With vigorous stirring, solution A is slowly added dropwise to B solution (material of Fluorenone pyridine organic ligands and nickel ion
The ratio of amount is 2～4:1), drip and be stirred vigorously complete follow-up continuing, and react 30～60min in 60～90 DEG C, reaction knot
By mixture ultrasonic disperse 30min, centrifugation after bundle, discard supernatant liquid, be precipitated thing；
By gained sediment respectively with deionized water and ethanol washing, ultrasonic disperse, centrifugation, discard upper solution to remove
Remove the ion dissociated and the organic ligand not being coordinated, then lower sediment thing is vacuum dried, obtains described Fluorenone pyridine nickel and receive
Rice bunch；
Described solvent is the one or any combination in propyl alcohol, isopropanol, ethanol；
Described nickel salt is one or more in nickel chloride, nickel acetate or nickel nitrate；
Entitled the 2 of described Fluorenone pyridine organic ligands, 7-bis-(4-pyridine)-9-Fluorenone, its molecular formula is C23H14N2O。
The preparation method of Fluorenone pyridine nickel nano-cluster the most according to claim 1, it is characterised in that described Fluorenone pyridine
Nickel nano-cluster is as effective catalyst catalysis carbon-carbon cross coupling reaction.
3. a Fluorenone pyridine nickel nano-cluster, it is characterised in that Fluorenone pyridine nickel nanometer according to claim 1 and 2
Bunch preparation method prepare.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102838442A (en) * | 2012-08-09 | 2012-12-26 | 烟台万润精细化工股份有限公司 | 9-alkenylfluorene derivatives and application thereof |
| CN103396356A (en) * | 2013-08-12 | 2013-11-20 | 宁波大学 | Spirofluorene copper pyridine micro-nano particle and preparation method thereof |
| CN104628628A (en) * | 2015-02-05 | 2015-05-20 | 宁波大学 | Fluorene pyridine nickle nano-particles and preparation method thereof |
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- 2016-04-29 CN CN201610280894.3A patent/CN105906670B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102838442A (en) * | 2012-08-09 | 2012-12-26 | 烟台万润精细化工股份有限公司 | 9-alkenylfluorene derivatives and application thereof |
| CN103396356A (en) * | 2013-08-12 | 2013-11-20 | 宁波大学 | Spirofluorene copper pyridine micro-nano particle and preparation method thereof |
| CN104628628A (en) * | 2015-02-05 | 2015-05-20 | 宁波大学 | Fluorene pyridine nickle nano-particles and preparation method thereof |
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