CN110845545A - Preparation method of bis (1, 5-cyclooctadiene) nickel - Google Patents
Preparation method of bis (1, 5-cyclooctadiene) nickel Download PDFInfo
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- CN110845545A CN110845545A CN201911198237.4A CN201911198237A CN110845545A CN 110845545 A CN110845545 A CN 110845545A CN 201911198237 A CN201911198237 A CN 201911198237A CN 110845545 A CN110845545 A CN 110845545A
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- cyclooctadiene
- nickel
- bis
- anhydrous
- inert gas
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- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 34
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000013078 crystal Substances 0.000 claims abstract description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011261 inert gas Substances 0.000 claims abstract description 14
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims abstract description 12
- 238000003825 pressing Methods 0.000 claims abstract description 12
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004576 sand Substances 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 4
- DRZUOPCJWAJOAG-UHFFFAOYSA-N CC(=O)C.CC(=O)C.[Ni] Chemical compound CC(=O)C.CC(=O)C.[Ni] DRZUOPCJWAJOAG-UHFFFAOYSA-N 0.000 claims description 3
- 208000005156 Dehydration Diseases 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003446 ligand Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of bis (1, 5-cyclooctadiene) nickel, which comprises the following steps: (1) adding 1, 5-cyclooctadiene into 0.5-1.0M anhydrous nickel diacetylacetonate tetrahydrofuran solution under anhydrous and oxygen-free conditions, cooling to-78 ℃, then dropwise adding an organic solution of diisobutyl aluminum hydride, and heating to-10-25 ℃ for reacting for 1-5 h after the addition is finished; (2) and (3) carrying out filter pressing under the protection of inert gas to obtain bis (1, 5-cyclooctadiene) nickel crystals, and then storing the crystals in a dark place under the atmosphere of inert gas. The method for preparing the bis (1, 5-cyclooctadiene) nickel has mild reaction conditions, is convenient for industrial mass production, and has high product purity and good yield.
Description
Technical Field
The invention belongs to the technical field of organic metal complex preparation, and particularly relates to a preparation method of bis (1, 5-cyclooctadiene) nickel.
Background
Bis (1, 5-cyclooctadiene) nickel as an organometallic complex is not only used directly as a highly efficient zero-valent nickel catalyst in many organic chemical reactions to promote or catalyze some reactions, such as: the bis (1, 5-cyclooctadiene) nickel can promote the carbon-carbon bond coupling reaction of brominated aromatic hydrocarbon to generate biphenyl under mild conditions, and can also catalyze the addition reaction of alkyne to generate bifunctional olefin derivatives. And because the 1, 5-cyclooctadiene ligand is easy to exchange and react with other ligands, the bis (1, 5-cyclooctadiene) nickel is also used as a common nickel source together with other ligands, and the bis (1, 5-cyclooctadiene) nickel is also used as a raw material for synthesizing a plurality of complex organic nickel complexes.
However, since bis (1, 5-cyclooctadiene) nickel is sensitive to light, humidity and air, is a flammable solid, and is difficult to prepare and store, few reports on effective synthesis of bis (1, 5-cyclooctadiene) nickel are made in China at present.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of bis (1, 5-cyclooctadiene) nickel, which is simple and low in cost.
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) adding 1, 5-cyclooctadiene into 0.5-1.0M tetrahydrofuran solution of anhydrous nickel diacetone under anhydrous and oxygen-free conditions, cooling to-78 ℃, then dropwise adding organic solution of diisobutyl aluminum hydride, and heating to-10-25 ℃ after adding for reaction for 1-5 h;
(2) and (3) carrying out filter pressing under the protection of inert gas to obtain bis (1, 5-cyclooctadiene) nickel crystals, and then storing the crystals in a dark place under the atmosphere of inert gas.
Preferably, the molar ratio of the anhydrous nickel diacetylacetonate to the 1, 5-cyclooctadiene to the diisobutylaluminum hydride is 1 (4.3-5.5) to (2.0-4.0).
Preferably, in the tetrahydrofuran solution of the anhydrous nickel diacetone, the tetrahydrofuran is subjected to water removal treatment.
Preferably, the organic solution of diisobutylaluminum hydride is a tetrahydrofuran solution of diisobutylaluminum hydride, a toluene solution of diisobutylaluminum hydride, or an n-hexane solution of diisobutylaluminum hydride.
Preferably, the filter pressing is carried out by adopting a sand plate filter pipe.
Preferably, the inert gas is nitrogen or argon.
The invention has the advantages that:
the preparation method of bis (1, 5-cyclooctadiene) nickel provided by the invention has the advantages of simple method, low cost, mild reaction conditions, convenience for industrial mass production, high product purity and good yield.
Detailed Description
Example 1
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 60mL of anhydrous tetrahydrofuran subjected to water removal treatment are mixed, 16mL (130.4 mmol) of 1, 5-cyclooctadiene is added into the mixture, the temperature is reduced to-78 ℃, 90mL of 1M tetrahydrofuran solution of diisobutylaluminum hydride (containing 90.0mmol of diisobutylaluminum hydride) is added dropwise into the mixture, and the temperature is increased to 0 ℃ after the addition is finished for reaction for 5 hours;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of nitrogen to obtain 7.43g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the inert gas atmosphere;
the yield of the example is 90% and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta is 4.30 (8H, s), 2.08 (s, 16H), the same characteristic parameters as reported in the prior art for bis (1, 5-cyclooctadiene) nickel.
Example 2
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 30mL of anhydrous tetrahydrofuran subjected to water removal treatment are mixed, 16mL (130.4 mmol) of 1, 5-cyclooctadiene is added into the mixture, the temperature is reduced to-78 ℃, 90mL of 1M tetrahydrofuran solution of diisobutylaluminum hydride (containing 90.0mmol of diisobutylaluminum hydride) is added dropwise into the mixture, and the temperature is increased to-10 ℃ for reaction for 5 hours after the addition is finished;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of nitrogen to obtain 7.62g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the atmosphere of inert gas;
the yield of the example is 92% and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta 4.30 (8H, s), 2.08 (s, 16H), as reported in the prior artThe characteristic parameters of the bis (1, 5-cyclooctadiene) nickel are the same.
Example 3
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 30mL of anhydrous tetrahydrofuran subjected to water removal treatment are mixed, 16mL (130.4 mmol) of 1, 5-cyclooctadiene is added into the mixture, the temperature is reduced to-78 ℃, 90mL of a 1M n-hexane solution of diisobutylaluminum hydride (containing 90.0mmol of diisobutylaluminum hydride) is dropwise added into the mixture, and the mixture is heated to 25 ℃ for reaction for 1h after the addition is finished;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of nitrogen to obtain 7.32g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the atmosphere of inert gas;
the yield of the example is 89%, and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta is 4.30 (8H, s), 2.08 (s, 16H), the same characteristic parameters as reported in the prior art for bis (1, 5-cyclooctadiene) nickel.
Example 4
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 60mL of anhydrous tetrahydrofuran subjected to dehydration treatment are mixed, 18mL (146.8 mmol) of 1, 5-cyclooctadiene are added into the mixture, the temperature is reduced to-78 ℃, 90mL of a 1M n-hexane solution of diisobutylaluminum hydride (containing 90mmol of diisobutylaluminum hydride) is added dropwise into the mixture, and the mixture is heated to 0 ℃ for reaction for 3 hours after the addition is finished;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of nitrogen to obtain 7.41g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the inert gas atmosphere;
the yield of the example is 90% and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta 4.30 (8H, s), 2.08 (s, 16H), vs. bis (1, 5-cyclooctane) reported in the prior artDiene) nickel have the same characteristic parameters.
Example 5
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 60mL of anhydrous tetrahydrofuran subjected to dehydration treatment are mixed, 20mL (163.1 mmol) of 1, 5-cyclooctadiene are added into the mixture, the temperature is reduced to-78 ℃, 120mL of a 1M n-hexane solution of diisobutylaluminum hydride (containing 120mmol of diisobutylaluminum hydride) is added dropwise into the mixture, and the mixture is heated to 0 ℃ for reaction for 5 hours after the addition is finished;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of argon to obtain 7.26g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the inert gas atmosphere;
the yield of the example is 88% and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta is 4.30 (8H, s), 2.08 (s, 16H), the same characteristic parameters as reported in the prior art for bis (1, 5-cyclooctadiene) nickel.
Example 6
A preparation method of bis (1, 5-cyclooctadiene) nickel comprises the following steps:
(1) under the anhydrous and oxygen-free conditions, 7.7g (30.0 mmol) of anhydrous nickel diacetylacetonate and 40mL of anhydrous tetrahydrofuran subjected to water removal treatment are mixed, 20mL (163.1 mmol) of 1, 5-cyclooctadiene is added into the mixture, the temperature is reduced to-78 ℃, 60mL of a 1M n-hexane solution of diisobutylaluminum hydride (containing 60mmol of diisobutylaluminum hydride) is added dropwise into the mixture, and the mixture is heated to 0 ℃ for reaction for 5 hours after the addition is finished;
(2) carrying out filter pressing by adopting a sand plate filter tube under the protection of argon to obtain 6.89g of bis (1, 5-cyclooctadiene) nickel crystal which is yellow crystal, and then storing in a dark place under the inert gas atmosphere;
the yield of the example is 83% and the product purity is 99%; making the obtained bis (1, 5-cyclooctadiene) nickel crystal into nuclear magnetic resonance hydrogen spectrum,1h NMR delta of 4.30 (8H, s), 2.08 (s, 16H), vs. bis (1, 5-cyclooctadiene) nickel reported in the prior artThe characterization parameters are the same.
Claims (6)
1. A preparation method of bis (1, 5-cyclooctadiene) nickel is characterized by comprising the following steps: the method comprises the following steps:
(1) adding 1, 5-cyclooctadiene into 0.5-1.0M anhydrous nickel diacetylacetonate tetrahydrofuran solution under anhydrous and oxygen-free conditions, cooling to-78 ℃, then dropwise adding an organic solution of diisobutyl aluminum hydride, and heating to-10-25 ℃ for reacting for 1-5 h after the addition is finished;
(2) and (3) carrying out filter pressing under the protection of inert gas to obtain bis (1, 5-cyclooctadiene) nickel crystals, and then storing the crystals in a dark place under the atmosphere of inert gas.
2. The process for preparing bis (1, 5-cyclooctadiene) nickel according to claim 1, wherein: the molar ratio of the anhydrous nickel diacetylacetonate, the 1, 5-cyclooctadiene and the diisobutylaluminum hydride is 1 (4.3-5.5) to 2.0-4.0.
3. The process for producing bis (1, 5-cyclooctadiene) nickel according to claim 1 or 2, characterized in that: in the tetrahydrofuran solution of the anhydrous nickel diacetone, the tetrahydrofuran is subjected to dehydration treatment.
4. The process for producing bis (1, 5-cyclooctadiene) nickel according to claim 1 or 2, characterized in that: the organic solution of diisobutyl aluminum hydride is tetrahydrofuran solution of diisobutyl aluminum hydride, toluene solution of diisobutyl aluminum hydride or n-hexane solution of diisobutyl aluminum hydride.
5. The process for producing bis (1, 5-cyclooctadiene) nickel according to claim 1 or 2, characterized in that: and a sand plate filter pipe is adopted for filter pressing during filter pressing.
6. The process for producing bis (1, 5-cyclooctadiene) nickel according to claim 1 or 2, characterized in that: the inert gas is nitrogen or argon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911198237.4A CN110845545A (en) | 2019-11-29 | 2019-11-29 | Preparation method of bis (1, 5-cyclooctadiene) nickel |
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| CN201911198237.4A CN110845545A (en) | 2019-11-29 | 2019-11-29 | Preparation method of bis (1, 5-cyclooctadiene) nickel |
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| CN110845545A true CN110845545A (en) | 2020-02-28 |
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| CN201911198237.4A Pending CN110845545A (en) | 2019-11-29 | 2019-11-29 | Preparation method of bis (1, 5-cyclooctadiene) nickel |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006264714A (en) * | 2005-03-23 | 2006-10-05 | Sumitomo Chemical Co Ltd | Storage container for metal-containing material |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006264714A (en) * | 2005-03-23 | 2006-10-05 | Sumitomo Chemical Co Ltd | Storage container for metal-containing material |
Non-Patent Citations (2)
| Title |
|---|
| DAMIAN J. KRYSAN等: "A New, Convenient Preparation of Bis(l,5-cyclooctadiene)nickel(0)", 《J. ORG. CHEM.》 * |
| MONTGOMERY, J.: "Product class 1: organometallic complexes of nickel", 《SCIENCE OF SYNTHESIS》 * |
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Application publication date: 20200228 |