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Cobalt complex, production method therefor, and catalyst for hydrosilylation reaction

A technology of hydrosilylation and manufacturing methods, applied in the direction of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, cobalt organic compounds, etc., can solve the problem of cobalt complexes with isonitrile ligands reported For example, there are no problems such as cobalt-isonitrile complex segregation, no catalyst utilization, etc., to achieve the effects of good solubility, easy handling, and high degree of crosslinking

Inactive Publication Date: 2020-05-08
KYUSHU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, there is also a problem that the selectivity of α-adducts and β-adducts is poor depending on the type of olefin.
[0024] Furthermore, catalysts for hydrosilylation reactions using isonitrile ligands have also been reported (Patent Documents 16 and 17), and there are also reports that isolated complexes can also be used, but there is no actual cobalt-isonitrile complex It is not clear whether a complex with a bond to silicon is formed
[0025] In addition, except for Non-Patent Document 12, there are no reported examples of cobalt complexes having an isonitrile ligand and a bond with silicon, and there are no examples of use as catalysts for the hydrosilylation reaction of olefins.

Method used

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  • Cobalt complex, production method therefor, and catalyst for hydrosilylation reaction
  • Cobalt complex, production method therefor, and catalyst for hydrosilylation reaction
  • Cobalt complex, production method therefor, and catalyst for hydrosilylation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193] [Example 1] cobalt complex {(EtO) 3 Si}Co(CNtBu) 4 Synthesis

[0194] Add cobalt pivalate (26.2mg, 0.1mmol), benzene (100μL), tert-butylisonitrile (67.8μL, 0.6mmol) and triethoxysilane (147μL, 0.8mmol) in the reaction vessel in order, at 25 It was stirred at ℃ for 12 hours. Then, the solvent of the reaction solution and remaining triethoxysilane were distilled off under reduced pressure. The obtained dried product was dissolved in pentane (about 2 mL), cooled to -35° C., and recrystallized to obtain {(EtO) 3 Si}Co(CNtBu) 4 (38.6 mg, 70%).

[0195] Mp=150℃(Celsius)

[0196] 1 H-NMR (400MHz, benzene-d 6 )δ: 4.37 (q, J=6.9, 6H), 1.57 (t, J=6.9, 9H), 1.24 (s, 36H).

[0197] 13 C-NMR (100MHz, benzene-d 6 )δ: 58.0, 55.1, 31.1, 19.5.

[0198] 29 Si-NMR (119MHz, benzene-d 6 )δ: 0.3.

[0199] IR(ATR): νCN=2120, 2030, 2008, 1982cm -1 .

[0200] C 26 h 51 O 3 N 4 Analytical calculated value of CoSi: C56.29, H9.27, N10.10; measured value: C56.18, H9.47, N9.95. ...

Embodiment 2

[0202] [Example 2] cobalt complex {(EtO) 3 Si}Co(CNAd) 4 Synthesis of (1)

[0203] Add cobalt pivalate (26.2 mg, 0.1 mmol), benzene (100 μL), adamantyl isonitrile (96.8 mg, 0.6 mmol), and triethoxysilane (147 μL, 0.8 mmol) in the reaction vessel in order, Stirring was carried out at 25°C for 12 hours. Then, the solvent of the reaction solution and remaining triethoxysilane were distilled off under reduced pressure. The dried product obtained was dissolved in diethyl ether (about 2 mL), cooled to -35°C, and recrystallized to obtain {(EtO) 3 Si}Co(CNAd) 4 (66.8 mg, 77%).

[0204] Mp=200℃(Celsius)

[0205] 1 H-NMR (400MHz, benzene-d 6)δ: 4.49 (q, J=6.9, 6H), 2.10 (br, 24H), 1.81 (br, 12H), 1.67 (t, J=6.9, 9H), 1.40 (m, 24H).

[0206] 13 C-NMR (100MHz, benzene-d 6 )δ: 171.2, 58.2, 55.6, 44.5, 36.1, 29.6, 19.7.

[0207] 29 Si-NMR (119MHz, benzene-d 6 )δ: 0.6.

[0208] IR(ATR): νCN=2143, 2109, 1990, 1955cm -1 .

[0209] C 50 H 75 O 3 N 4 Analytical calculated va...

Embodiment 3

[0211] [Example 3] Cobalt complex {Me 2 (Me 3 SiO)Si}Co(CNtBu) 4 Synthesis

[0212] In a reaction vessel, press cobalt pivalate (26.2 mg, 0.1 mmol), benzene (100 μL), tert-butylisonitrile (67.8 μL, 0.6 mmol), 1,1,1,3,3-pentamethyldisiloxane Alkane (157 μL, 0.8 mmol) was added sequentially and stirred at 25° C. for 12 hours. Then, the solvent of the reaction solution and the remaining 1,1,1,3,3-pentamethyldisiloxane were distilled off under reduced pressure. The obtained dried product was dissolved in pentane (about 2 mL), cooled to -35°C, and recrystallized to obtain {Me 2 (Me 3 SiO)Si}Co(CNtBu) 4 (30.0 mg, 56%).

[0213] Mp=120°C (degree Celsius)

[0214] 1 H-NMR (400MHz, benzene-d 6 )δ: 1.50(s, 9H), 1.27(s, 6H), 1.20(s, 36H).

[0215] 13 C-NMR (100MHz, benzene-d 6 )δ: 170.9, 55.0, 31.1, 28.2, 8.75.

[0216] 29 Si-NMR (119MHz, benzene-d 6 )δ: 45.7, 0.2.

[0217] IR(ATR): νCN=2121, 1990, 1939 cm -1 .

[0218] C 25 H 51 O 3 N 4 CoSi 2 Analytical calculat...

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Abstract

A cobalt complex represented by formula (1), which exhibits excellent catalytic activity in hydrosilylation reactions and is excellent in terms of handleability and solubility in silicones. {In formula (1), R1 to R3 each independently represent a hydrogen atom or a C1-30 monovalent organic group which may have been substituted by a halogen atom and may be separated by one or more atoms selected from among oxygen, nitrogen, and silicon atoms, and at least one pair among R1 to R3 may be bonded together to form a C1-30 bridged substituent which may be optionally separated by one or more atoms selected from among oxygen, nitrogen, and silicon atoms; the L moieties each independently represent an isocyanide ligand represented by the formula CN-R4 (2) (wherein R4 represents a C1-30 monovalent organic group which may have been substituted by a halogen atom and may be separated by one or more atoms selected from among oxygen, nitrogen, sulfur, and silicon atoms); and n is 4}.

Description

technical field [0001] The present invention relates to a cobalt complex, a method for producing the same, and a catalyst for hydrosilylation reaction. A catalyst for the hydrosilylation reaction of the cobalt complex. Background technique [0002] For compounds having carbon-carbon double bonds and carbon-carbon triple bonds, the hydrosilylation reaction of addition of Si-H functional compounds is a useful means for synthesizing organosilicon compounds, and it is also an industrially important synthesis reaction. [0003] As catalysts for this hydrosilylation reaction, Pt, Pd, and Rh compounds are known, and among them, Pt compounds typified by Speier catalyst and Karstedt catalyst are most used. [0004] As a problem in the reaction using a Pt compound as a catalyst, a side reaction in which an olefin internally rearranges occurs when a Si—H functional compound is added to a terminal olefin. Since this system does not show addition reactivity to internal olefins and unre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00B01J31/22C07F7/08C07F7/18C07F15/06
CPCB01J31/22C07F15/06C07F7/0829C07F7/08C07F7/18C07F19/00C08G77/08
Inventor 永岛英夫真川敦嗣野田大辅作田晃司
Owner KYUSHU UNIV
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