CN114621279A - Preparation method for aryl silane dimer compound through aryl silane self-coupling synthesis under photocatalysis - Google Patents
Preparation method for aryl silane dimer compound through aryl silane self-coupling synthesis under photocatalysis Download PDFInfo
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- CN114621279A CN114621279A CN202210409201.1A CN202210409201A CN114621279A CN 114621279 A CN114621279 A CN 114621279A CN 202210409201 A CN202210409201 A CN 202210409201A CN 114621279 A CN114621279 A CN 114621279A
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- -1 aryl silane dimer compound Chemical class 0.000 title claims abstract description 33
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 17
- 238000005859 coupling reaction Methods 0.000 title claims abstract description 16
- 238000010168 coupling process Methods 0.000 title claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
- 230000001699 photocatalysis Effects 0.000 title claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
- 238000007146 photocatalysis Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910008045 Si-Si Inorganic materials 0.000 claims abstract description 7
- 229910006411 Si—Si Inorganic materials 0.000 claims abstract description 7
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 6
- 239000011941 photocatalyst Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 13
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical group [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 238000005266 casting Methods 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 150000004756 silanes Chemical class 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- MHSHAEXCPBUGDM-UHFFFAOYSA-N (4-chlorophenyl)-diphenylsilane Chemical compound C1=CC(Cl)=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 MHSHAEXCPBUGDM-UHFFFAOYSA-N 0.000 description 1
- NRBDIQMFDLFULN-UHFFFAOYSA-N (4-methylphenyl)-[(4-methylphenyl)-diphenylsilyl]-diphenylsilane Chemical compound C1=CC(C)=CC=C1[Si]([Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRBDIQMFDLFULN-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- OIKHZBFJHONJJB-UHFFFAOYSA-N dimethyl(phenyl)silicon Chemical compound C[Si](C)C1=CC=CC=C1 OIKHZBFJHONJJB-UHFFFAOYSA-N 0.000 description 1
- 229960001483 eosin Drugs 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical group [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- OKHRRIGNGQFVEE-UHFFFAOYSA-N methyl(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](C)C1=CC=CC=C1 OKHRRIGNGQFVEE-UHFFFAOYSA-N 0.000 description 1
- JNZRJYXUMDPPRK-UHFFFAOYSA-N methyl-[methyl(diphenyl)silyl]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si]([Si](C)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNZRJYXUMDPPRK-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ZMHATUZXFSOVSC-UHFFFAOYSA-N triphenyl(triphenylsilyl)silane Chemical compound C1=CC=CC=C1[Si]([Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZMHATUZXFSOVSC-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0231—Halogen-containing compounds
- B01J31/0232—Halogen-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0228
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
A preparation method of aryl silane dimer compounds through aryl silane self-coupling synthesis under photocatalysis is characterized in that a non-metal photosensitizer is used as a photocatalyst, and a tri-substituted aryl silane compound is placed in a solvent under the irradiation of light and air environment to generate a Si-Si bond coupling reaction, so that the aryl silane dimer compounds are generated. In the invention, under the air environment, a simple nonmetal photosensitizer is used for catalyzing the self-coupling of the tri-substituted aryl silane compound to form Si-Si coupling reaction, and a series of silane dimers can be realized under mild conditions and with high yield. The method has no oxidant, is environment-friendly, has high atom economy and simple and convenient post-treatment, and has application prospect in many fields such as adhesive, paint, casting adhesive and the like.
Description
Technical Field
The invention belongs to the fields of organic chemical industry, organic synthesis and photocatalysis, relates to preparation of aryl silane dimer compounds, and particularly relates to a method for synthesizing aryl silane dimer compounds by self-coupling of three-level aryl silane compounds under the photocatalysis of a photosensitizer.
Background
The silane can react with a plurality of inorganic materials and organic materials and has multiple functions. The uniqueness of organosilanes as coupling agents, crosslinkers and surface modifiers has led to their widespread use in many areas such as adhesives, coatings, foundry binders and the like. The formation of Si — Si is an important step in the synthesis of disilanes, oligosilanes and polysilanes that have optoelectronic, photoreactive properties and are of interest. Therefore, the development of a method for synthesizing the silane dimer compound has important practical value.
At present, the synthesis method of silane dimer compounds under the catalysis of alkali metal or iron compounds has been reported. For example: in [ CpFe (CO) ]2Me]In the catalytic system, a Si-Si bond is constructed by self-coupling of dimethyl phenyl silane so as to synthesize the silane dimer compound in a one-step catalytic manner.
Therefore, the existing silane dimer compound synthesis needs to be catalyzed by alkali metal or metal compound, but the metal pollutes the environment, the atom economy is general, and most of reaction raw materials and catalysts are expensive and not easy to obtain, so that the industrial production of the silane dimer compound is limited. At present, no published documents for forming silane dimer compounds by utilizing a photosensitizer to perform photocatalytic Si-Si bond coupling in an air environment exist at home and abroad.
Disclosure of Invention
The invention aims to provide a method for preparing an aryl silane dimer compound by self-coupling a tri-substituted aryl silane compound under the catalysis of a photosensitizer. The method takes a non-metal photosensitizer as a catalyst, and can lead the tertiary aryl silane compound to generate the required aryl silane dimer compound at room temperature with high yield under the conditions of air environment and light irradiation.
In order to achieve the purpose, the invention adopts the technical scheme that: a preparation method of aryl silane dimer compounds through aryl silane self-coupling synthesis under photocatalysis is characterized in that a non-metal photosensitizer is used as a photocatalyst, a trisubstituted aryl silane compound is placed in a solvent under the irradiation of light and air environment to generate a Si-Si bond coupling reaction, and the aryl silane dimer compounds are generated, wherein the reaction general formula is as follows:
wherein the substrate trisubstituted aryl silane compound has the general formula
Wherein R is phenyl, tolyl, halophenyl or methyl.
Preferably, the photosensitizer is eosin (tetrabromo fluorescein); the solvent is DCM; the light wavelength was 430 nm. The reaction temperature is room temperature, and the reaction time is 1 h; the molar ratio of the tri-substituted aryl silane compound to the photosensitizer at the beginning of the reaction is 1: 0.1, 2mL of solvent.
In the air environment, the simple non-metal photosensitizer is used for catalyzing the self-coupling of the tri-substituted aryl silane compound to form the Si-Si coupling reaction, and the used photosensitizer is cheap and easy to obtain, is easy to recover and has no pollution. The invention can realize a series of silane dimers under mild conditions with high yield, does not participate in an oxidant, is environment-friendly, has high atom economy and simple and convenient post-treatment, and has application prospect in a plurality of fields such as adhesives, coatings, casting adhesives and the like.
Detailed Description
The following examples will help to understand the present invention, but the contents of the present invention are not limited thereto.
Example 1: 1,1,1,2,2, 2-hexaphenyldisilane
78.123mg (0.3mmol) of triphenylsilane as a substrate, 4.98mg (0.03mmol) of EOSIN Y as a photosensitizer and 2mL of DCM as a solvent were added to a photoreaction sealed tube under an air atmosphere. Then the sealed tube is put into a 430nm photoreactor and reacted for 1h at room temperature. After the reaction, the reaction mixture was subjected to rotary evaporation and separation by silica gel column chromatography (eluent ethyl acetate/petroleum ether: 1/8) to give 77.0mg of a colorless oily liquid with a yield of 98.5%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.62(t, J ═ 16.0Hz,2H),7.38(t, J ═ 8.0Hz,2H),3.26-3.21(m,4H),2.42(s,3H),1.13(t, J ═ 8.0Hz,6H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 140.19,139.21,133.12,128.94,127.43,124.17,42.17,21.52,14.28, HRMS m/z, found 519.1996, and the structural formula is shown in the specification
Example 2: 1,1,2, 2-tetraphenyl-1, 2-di-p-tolyldisilane
82.233mg (0.3mmol) of substrate p-tolyldiphenylsilane and 4.98mg of photosensitizer EOSIN Y
(0.03mmol) and 2mL of DCM solvent were added to the photoreaction tube under air atmosphere. Then the sealed tube is put into a 430nm photoreactor to react for 1h at room temperature. After the reaction was completed, the reaction mixture was subjected to rotary evaporation and then to silica gel column chromatography (eluent: ethyl acetate/petroleum ether: 1/8), whereby 80.2mg of a colorless oily liquid was obtained in a yield of 97.9%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.47-7.45(m,8H),7.35(d, J ═ 7.6Hz,4H),7.28(t, J ═ 7.6Hz,4H),7.20(t, J ═ 7.6Hz,8H),7.03(d, J ═ 7.6Hz,4H),2.23(s,6H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 140.18,135.48,135.23,135.13,131.63,130.10,128.87,127.99,21.75, HRM S: m/z, found:547.2230, and has the structural formula:
example 3: 1,1,2, 2-tetraphenyl-1, 2-di-m-tolyldisilane
82.233mg (0.3mmol) of m-tolyldiphenylsilane as a substrate, 4.98mg (0.03mmol) of EOSIN Y as a photosensitizer and 2mL of DCM as a solvent were added to the photoreaction vial under an air atmosphere. Then the sealed tube is put into a 430nm photoreactor and reacted for 1h at room temperature. After the reaction, the reaction mixture was subjected to rotary evaporation and silica gel column chromatography (eluent ethyl acetate/petroleum ether: 1/8) to give 79.2mg of a pale yellow oily liquid with a yield of 96.7%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.66-7.64(m,8H),7.50-7.44(m,8H),7.37(t, J ═ 7.6Hz,8H),7.29(d, J ═ 5.2Hz,4H),2.34(s,6H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 137.34,135.57,135.33,135.10,135.01,132.22,130.99,130.08,127.95,127.91,21.58, HRMS m/z, found 547.2213, and the structural formula is:
example 4: 1, 2-bis (4-chlorophenyl) -1,1,2, 2-tetraphenyl-disilane
88.452mg (0.3mmol) of p-chlorophenyl diphenylsilane as a substrate, 4.98mg (0.03mmol) of EOSIN Y as a photosensitizer and 2mL of DCM as a solvent were added to the photoreaction vial under an air atmosphere. Then the sealed tube is put into a 430nm photoreactor and reacted for 1h at room temperature. After the reaction, the reaction mixture was subjected to rotary evaporation and then to silica gel column chromatography (eluent: ethyl acetate/petroleum ether: 1/8) to obtain 85.7mg of a pale yellow oily liquid with a yield of 97.5%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.41(dd, J ═ 7.6,0.8Hz,8H),7.35(d, J ═ 8.0Hz,4H),7.30(d, J ═ 7.6Hz,4H),7.22-7.16(m,12H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 135.42,135.30,134.25,133.85,133.46,132.36,129.20,127.10,126.92, HRMS m/z, found 587.1227, and has the structural formula:
example 5: 1, 2-bis (3-fluorophenyl) -1,1,2, 2-tetraphenyl-disilane
83.517mg (0.3mmol) of m-fluorophenyl diphenyl silane as a substrate, 4.98mg (0.03mmol) of EOSIN Y as a photosensitizer and 2mL of DCM as a solvent are added into a photoreaction sealed tube under an air environment. Then the sealed tube is put into a 430nm photoreactor and reacted for 1h at room temperature. After the reaction, the reaction mixture was subjected to rotary evaporation and then to silica gel column chromatography (eluent: ethyl acetate/petroleum ether: 1/8) to obtain 79.8mg of a pale yellow oily liquid with a yield of 95.6%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.44(d, J ═ 6.8Hz,8H),7.30(t, J ═ 7.6Hz,4H),7.21(t, J ═ 7.6Hz,10H),7.18-7.14(m,4H),6.96(td, J ═ 8.0,1.6Hz,2H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 162.63(d, J-249.5 Hz),138.40(d, J-4.0 Hz),135.05,134.54,130.66(d, J-3.0 Hz),130.39,129.87(d, J-7.0 Hz),128.10,121.38(d, J-19.1 Hz),117.14(d, J-21.0 Hz) and HRMS: m/z, found:555.2338
Example 6: 1, 2-dimethyl-1, 1,2, 2-tetraphenyl-disilane
60.123mg (0.3mmol) of diphenylmethylsilane as a substrate, 4.98mg (0.03mmol) of EOSIN Y as a photosensitizer and 2mL of DCM as a solvent were added to the photoreaction vial under an air atmosphere. Then the sealed tube is put into a 430nm photoreactor and reacted for 1h at room temperature. After the reaction, the reaction mixture was subjected to rotary evaporation and then to silica gel column chromatography (ethyl acetate/petroleum ether: 1/8 as an eluent) to obtain 55.614mg of a pale yellow oily liquid with a yield of 92.5%.
The obtained liquid is subjected to hydrogen spectrum:1H NMR(400MHz,CDCl3): δ 7.59(dd, J ═ 8.0,1.2Hz,8H),7.44-7.40(m,4H),7.36(t, J ═ 7.2Hz,8H),0.647(s,6H), carbon spectrum:13C NMR(101MHz,CDCl3): delta 137.69,134.13,129.72,127.88, -0.41, HRM S: m/z, found:395.2137, and has the structural formula:
Claims (6)
1. a preparation method of aryl silane dimer compounds through aryl silane self-coupling synthesis under photocatalysis is characterized in that a non-metal photosensitizer is used as a photocatalyst, a tri-substituted aryl silane compound is placed in a solvent under the irradiation of light and air environment to generate Si-Si bond coupling reaction, and the aryl silane dimer compounds are generated according to the following reaction formula:
wherein the substrate trisubstituted aryl silane compound has the general formula
Wherein R is phenyl, tolyl, halophenyl or methyl.
2. The method of claim 1, wherein the photosensitizer is EOSIN Y.
3. The process of claim 1, wherein the solvent is DCM.
4. The method of claim 1, wherein the light wavelength is 430 nm.
5. The method of claim 1, wherein the reaction temperature is room temperature.
6. The method of claim 1, wherein the reaction is initiated with a molar ratio of trisubstituted aryl silane compound to photosensitizer of 1: 0.1.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725342A (en) * | 1986-11-10 | 1988-02-16 | Yale University | Photochemical dimerization and functionalization of alkanes, ethers, primary alcohols and silanes |
| JPH01203396A (en) * | 1988-02-06 | 1989-08-16 | Agency Of Ind Science & Technol | Production of disilanes |
| US5540830A (en) * | 1994-03-09 | 1996-07-30 | Osaka Gas Company Limited | Method for producing disilanes |
| JP2003277387A (en) * | 2002-03-20 | 2003-10-02 | Osaka Gas Co Ltd | Method for producing disilane |
| US20090112013A1 (en) * | 2007-10-31 | 2009-04-30 | Hiroshi Nakazawa | Preparation of si-si bond-bearing compounds |
| JP2014181212A (en) * | 2013-03-19 | 2014-09-29 | Yokohama National Univ | Method for manufacturing silicon compound and catalyst composition |
| CN107955031A (en) * | 2017-12-05 | 2018-04-24 | 南京工业大学 | Method for continuously preparing disilane compounds by using micro-reaction device |
| CN110669066A (en) * | 2019-10-15 | 2020-01-10 | 徐州医科大学 | Disilane and preparation method thereof |
| CN112110950A (en) * | 2020-08-17 | 2020-12-22 | 杭州师范大学 | Preparation method of disilane |
-
2022
- 2022-04-19 CN CN202210409201.1A patent/CN114621279A/en not_active Withdrawn
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725342A (en) * | 1986-11-10 | 1988-02-16 | Yale University | Photochemical dimerization and functionalization of alkanes, ethers, primary alcohols and silanes |
| JPH01203396A (en) * | 1988-02-06 | 1989-08-16 | Agency Of Ind Science & Technol | Production of disilanes |
| US5540830A (en) * | 1994-03-09 | 1996-07-30 | Osaka Gas Company Limited | Method for producing disilanes |
| JP2003277387A (en) * | 2002-03-20 | 2003-10-02 | Osaka Gas Co Ltd | Method for producing disilane |
| US20090112013A1 (en) * | 2007-10-31 | 2009-04-30 | Hiroshi Nakazawa | Preparation of si-si bond-bearing compounds |
| JP2014181212A (en) * | 2013-03-19 | 2014-09-29 | Yokohama National Univ | Method for manufacturing silicon compound and catalyst composition |
| CN107955031A (en) * | 2017-12-05 | 2018-04-24 | 南京工业大学 | Method for continuously preparing disilane compounds by using micro-reaction device |
| CN110669066A (en) * | 2019-10-15 | 2020-01-10 | 徐州医科大学 | Disilane and preparation method thereof |
| CN112110950A (en) * | 2020-08-17 | 2020-12-22 | 杭州师范大学 | Preparation method of disilane |
Non-Patent Citations (4)
| Title |
|---|
| AYA YOSHIMURA等: "Photoinduced Reductive Coupling of Organochlorosilanes with SmI2/Sm", HETEROATOM CHEMISTRY, vol. 25, no. 6, pages 684 - 689 * |
| GUOQIAO LAI等: "Direct construction of silicon–silicon bond by using the low-valent titanium reagent", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 692, pages 3559 - 3562, XP022133076, DOI: 10.1016/j.jorganchem.2007.04.008 * |
| MASUMI ITAZAKI等: "Iron-Catalyzed Dehydrogenative Coupling of Tertiary Silanes", ANGEW. CHEM. INT. ED., vol. 48, pages 3313 - 3316 * |
| PEI HE等: "Visible-Light-Induced Aerobic Oxidation of Tertiary Silanes to Silanols using Molecular Oxygen as an Oxidant", SYNTHESIS, vol. 55, pages 765 - 772 * |
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