CN108409770A - The method for preparing borate based on anilino- lithium - Google Patents
The method for preparing borate based on anilino- lithium Download PDFInfo
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- CN108409770A CN108409770A CN201810336794.7A CN201810336794A CN108409770A CN 108409770 A CN108409770 A CN 108409770A CN 201810336794 A CN201810336794 A CN 201810336794A CN 108409770 A CN108409770 A CN 108409770A
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- ketone
- lithium
- anilino
- borine
- hydroboration
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- IFOBAKIQHNOSRE-UHFFFAOYSA-N lithium;phenylazanide Chemical compound [Li+].[NH-]C1=CC=CC=C1 IFOBAKIQHNOSRE-UHFFFAOYSA-N 0.000 title claims abstract description 31
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 11
- 229910000085 borane Inorganic materials 0.000 claims abstract description 35
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000006197 hydroboration reaction Methods 0.000 claims abstract description 29
- 150000002576 ketones Chemical class 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- -1 heterocyclic ketone Chemical class 0.000 claims abstract description 14
- 150000008365 aromatic ketones Chemical group 0.000 claims abstract description 12
- 230000018044 dehydration Effects 0.000 claims abstract description 11
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 3
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical group CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 16
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical group CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000005311 nuclear magnetism Effects 0.000 description 6
- YOMBUJAFGMOIGS-UHFFFAOYSA-N 2-fluoro-1-phenylethanone Chemical compound FCC(=O)C1=CC=CC=C1 YOMBUJAFGMOIGS-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0252—Nitrogen containing compounds with a metal-nitrogen link, e.g. metal amides, metal guanidides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses the methods for preparing borate based on anilino- lithium, under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, catalyst aniline base lithium is then added, is uniformly mixed, add ketone, hydroboration occurs, is exposed in air and terminates reaction, obtain borate；The ketone is aromatic ketone or heterocyclic ketone.Present invention firstly discovers that anilino- lithium extremely can efficiently be catalyzed aromatic ketone or heterocyclic ketone occurs hydroboration with borine, new scheme is provided to prepare borate with borine generation hydroboration using carbonyls.
Description
Technical field
The application of anilino- lithium of the present invention, and in particular to the method that borate is prepared based on anilino- lithium.
Technical background
Hydroboration research for unsaturated bond all has important meaning for modern industry and Synthetic Organic Chemistry
Justice is widely paid close attention to so as to cause researcher.
Various catalyst have been used for the hydroboration of ketone, especially in recent years, about this kind of reaction
It reports many.Since under no catalysts conditions, the hydroboration of carbonyls is difficult to occur.So for this one kind
The research emphasis of reaction exactly develops efficient catalyst system and catalyzing.But the catalyst system and catalyzing reported at present, catalyst are all opposite
Costliness or reaction condition are more harsh.
So the catalyst system and catalyzing for developing the hydroboration of efficient catalytic ketone under new temperate condition is particularly urgent.
Invention content
The goal of the invention of the present invention is to provide the application of anilino- lithium, i.e., using anilino- lithium be effective catalyst be catalyzed ketone and
Borine occurs hydroboration and prepares borate；The anilino- lithium chemical formula is：PhNHLi, chemical structural formula are as follows：
To achieve the above object of the invention, the technical solution adopted by the present invention is：
A method of borate is prepared based on anilino- lithium, is included the following steps：
Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter catalyst aniline base lithium, be uniformly mixed, add ketone, hydroboration occurs, is exposed in air and terminates reaction, obtain boron
Acid esters；The ketone is aromatic ketone or heterocyclic ketone.
The present invention further discloses anilino- lithium in catalysis ketone and the application in borine hydroboration；The ketone is
Aromatic ketone or heterocyclic ketone.
The invention also discloses the methods of anilino- lithium catalysis ketone and borine generation hydroboration, include the following steps：
Under anhydrous and oxygen-free environment, under atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter anilino- lithium, be uniformly mixed, add ketone, hydroboration occurs.
In above-mentioned technical proposal, the chemical structure of general formula of the aromatic ketone is as follows：
Wherein R is one kind in electron-withdrawing group or electron donating group, can be selected from halogen, methyl；
The heterocyclic ketone is selected from 2- acetyl thiophenes；
The borine is selected from pinacol borine；
The dosage of the catalyst is the 0.1% of ketone mole, and the molar ratio of ketone and borine is 1: 1.1；
The temperature of hydroboration is room temperature, and the reaction time is 20 minutes.
Above-mentioned technical proposal can indicate as follows：
R1、R2Come from raw ketone.
Due to the application of the above technical scheme, the present invention has the following advantages compared with prior art：
1. present invention firstly discovers that anilino- lithium extremely can efficiently be catalyzed aromatic ketone or heterocyclic ketone occurs hydroboration with borine
Reaction provides new scheme to prepare borate with borine generation hydroboration using carbonyls.
2. high (the catalyst use of catalytic activity that hydroboration occurs with borine for anilino- lithium catalysis ketone disclosed by the invention
Amount is only that 0.1%), reaction condition is mild (room temperature), and the reaction time is short (20min), and reaction yield is high, and reaction is simple controllable, after
Processing is simple, and reaction uses solvent-free system, reduces the pollution to environment.
3. catalyst disclosed by the invention is for the aromatic ketone of different the position of substitution, different electronic effects and to heterocyclic ketone
There is preferable universality, the boric acid ester compound to obtain different substituents structure provides more selections.
Specific implementation mode
The present invention is described further with reference to embodiment：
Embodiment one：Anilino- lithium is catalyzed acetophenone and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
0.117 mL acetophenones, mixture are stirred at room temperature, and after reacting 20 min, nuclear-magnetism yield is 99%, are removed under reduced pressure later a small amount of
Tetrahydrofuran and excessive borine to get to corresponding pinacol borate.C6H5CH(CH3)OB(OC(CH3)2C(CH3)2O)。1H NMR (400 MHz, CDCl3) δ 7.38-7.21 (m, 5H, Ar-H), 5.24 (q, J = 6.5 Hz,
1H, OCH), 1.49 (d, J = 6.5 Hz, 3H, CH3), 1.22 (d, J = 11.9 Hz, 12H, CH3)。 13C
NMR (101 MHz, CDCl3) δ 144.09 (Ar-C), 127.71 (Ar-C), 126.62 (Ar-C), 124.86
(Ar-C), 82.26 (OC), 72.10 (OCH), 24.98 (CH3), 24.07 (d, J = 4.5 Hz, CH3)。
Embodiment two：Anilino- lithium is catalyzed to fluoro acetophenone and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
Fluoro acetophenone, mixture is stirred at room temperature in 0.1208 mL, and after reacting 20 min, nuclear-magnetism yield is 99%, and decompression later removes
Go a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate.1H NMR (400 MHz, CDCl3)
δ 7.35-7.30 (m, 2H, Ar-H), 7.02-6.96 (m, 2H, Ar-H), 5.22 (q, J = 6.4 Hz, 1H,
OCH), 1.47 (d, J = 6.5 Hz, 3H, CH3), 1.22 (d, J = 11.6 Hz, 12H, CH3)。 13C NMR
(101 MHz, CDCl3) δ 161.94 (ds, Ar-C), 140.34 (d, J = 3.1 Hz, Ar-C), 127.02
(d, J = 8.0 Hz, Ar-C), 114.93 (ds, Ar-C), 82.80 (OC), 72.00 (OCH), 25.40
(CH3), 24.52 (d, J = 6.1 Hz, CH3)。
Embodiment three：Fluoro acetophenone and pinacol borine hydroboration between the catalysis of anilino- lithium
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
Fluoro acetophenone between 0.1226 mL, mixture are stirred at room temperature, and after reacting 20 min, nuclear-magnetism yield is 99%, and decompression later removes
Go a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate.1H NMR (400 MHz, CDCl3)
δ 7.29-7.24 (m, 1H, Ar-H), 7.12-7.08 (m, 2H, Ar-H), 6.94-6.89 (m, 1H, Ar-H),
5.23 (q, J = 6.4 Hz, 1H, OCH), 1.48 (d, J = 6.5 Hz, 3H, CH3), 1.23 (d, J =
11.4 Hz, 12H, CH3)。13C NMR (101 MHz, CDCl3) δ 162.85 (ds, Ar-C), 147.26 (d, J
= 6.9 Hz, Ar-C), 129.67 (d, J = 8.2 Hz, Ar-C), 120.88 (d, J = 2.8 Hz, Ar-C),
113.87 (ds, Ar-C), 112.33 (ds, Ar-C), 82.87 (OC), 71.95 (d, J = 1.8 Hz, OCH),
25.30 (CH3), 24.52 (d, J = 4.2 Hz, CH3)。
Example IV：Anilino- lithium is catalyzed parachloroacetophenone and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
0.1297 mL parachloroacetophenones, mixture are stirred at room temperature, and after reacting 20 min, nuclear-magnetism yield is 99%, and decompression later removes
Go a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate.1H NMR (400 MHz, CDCl3)
δ 7.31-7.26 (m, 4H, Ar-H), 5.21 (q, J = 6.4 Hz, 1H, OCH), 1.46 (d, J = 6.5
Hz, 3H, CH3), 1.22 (d, J = 11.4 Hz, 12H, CH3)。 13C NMR (101 MHz, CDCl3) δ
142.62 (Ar-C), 132.26 (Ar-C), 127.83 (Ar-C), 126.29 (Ar-C), 82.35 (OC), 71.45
(OCH), 24.87 (CH3), 24.04 (d, J = 4.7 Hz, CH3)。
Embodiment five：Anilino- lithium is catalyzed melilotal and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
0.1335 mL melilotal, mixture are stirred at room temperature, and after reacting 20 min, nuclear-magnetism yield is more than 99%, subtracts later
Pressure removes a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate.1H NMR (400 MHz,
CDCl3) δ 7.26-7.24 (m, 2H, Ar-H), 7.11-7.13 (m, 2H, Ar-H), 5.21 (q, J = 6.4
Hz, 1H, OCH), 2.32 (s, 3H, Ar-CH3), 1.47 (d, J = 6.5 Hz, 3H, CH3), 1.22 (d, J
= 10.4 Hz, 12H, CH3)。 13C NMR (101 MHz, CDCl3) δ 141.17 (Ar-C), 136.17 (Ar-C),
128.38 (Ar-C), 124.82 (Ar-C), 82.21 (OC), 71.96 (OCH), 24.99 (CH3), 24.08 (d,J = 3.7 Hz, CH3), 20.61 (s, Ar-CH3)。
Anilino- lithium is replaced with to the amido lithium compound of formula I, it is virtually impossible to obtain product, yield is less than 7%.
Embodiment six：Anilino- lithium is catalyzed to 2- acetyl thiophenes and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran solution that 20ul anilino- lithiums are added of argon gas protection
(0.05M) (0.1 mol% dosages) is then added 0.1596 mL borines with syringe, is uniformly mixed, then be added with syringe
0.1097 mL2- acetyl thiophenes, mixture are stirred at room temperature, and after reacting 20 min, nuclear-magnetism yield is 99%, and decompression later removes
Go a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate.1H NMR (400 MHz, CDCl3)
δ 7.20-7.18 (m, 1H, Ar-H), 6.97-6.91 (m, 2H, Ar-H), 5.48 (q, J = 6.4 Hz, 1H,
OCH), 1.60 (d, J = 6.4 Hz, 3H, CH3), 1.24 (d, J = 4.9 Hz, 12H, CH3)。 13C NMR
(101 MHz, CDCl3) δ 147.72 (Ar-C), 125.90 (Ar-C), 123.63 (Ar-C), 122.79 (Ar-
C), 82.44 (OC), 68.15 (OCH), 24.58 (CH3), 24.09 (d, J = 9.8 Hz, CH3)。
Although belonging to carbonyls, ketone and aldehyde have different reaction properties, this is common sense, and the prior art exists simultaneously
Using keto-aldehyde as raw material, but only there is a situation where a kind of raw materials to react；Electron donating group can weaken the electropositive of carbonyl carbon, to cut
The nucleophilic addition activity of weak carbonyl, aromatic aldehyde is since conjugation reduces carbonyl activity, to different the position of substitution, different electronic effects
Aromatic compound and fatty compound have and larger react difference.Present invention firstly discovers that anilino- lithium can be with high
Catalytic activity is catalyzed aromatic ketone, the hydroboration of heterocyclic ketone, and has very wide substrate usage range.Cheap urges
Agent and lower catalyst amount, mild catalytic condition provide possibility for industrial applications.
Claims (10)
1. a kind of method preparing borate based on anilino- lithium, includes the following steps：
Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter catalyst aniline base lithium, be uniformly mixed, add ketone, hydroboration occurs, is exposed in air and terminates reaction, obtain boron
Acid esters；The ketone is aromatic ketone or heterocyclic ketone.
2. the method for preparing borate based on anilino- lithium according to claim 1, which is characterized in that the change of the aromatic ketone
It is as follows to learn general structure：
Wherein R is one kind in electron-withdrawing group or electron donating group；
The heterocyclic ketone is selected from 2- acetyl thiophenes.
3. the method for preparing borate based on anilino- lithium according to claim 1, which is characterized in that the borine is selected from frequency
Any alcohol borine.
4. the method for preparing borate based on anilino- lithium according to claim 1, which is characterized in that the use of the catalyst
Amount is the 0.1% of ketone mole, and the molar ratio of ketone and borine is 1: 1.1.
5. the method for preparing borate based on anilino- lithium according to claim 1, which is characterized in that the temperature of hydroboration
Degree is room temperature, and the time is 20 minutes.
6. anilino- lithium is in catalysis ketone and the application in borine hydroboration；The ketone is aromatic ketone or heterocyclic ketone.
7. application according to claim 6, which is characterized in that the hydroboration includes the following steps：
Under anhydrous and oxygen-free environment, under atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then adds
Enter anilino- lithium, be uniformly mixed, add ketone, hydroboration occurs.
8. application according to claim 6, which is characterized in that the chemical structure of general formula of the aromatic ketone is as follows：
Wherein R is one kind in electron-withdrawing group or electron donating group；
The heterocyclic ketone is selected from 2- acetyl thiophenes；
The borine is selected from pinacol borine.
9. application according to claim 6, which is characterized in that the dosage of the anilino- lithium is the 0.1% of ketone mole,
The molar ratio of ketone and borine is 1: 1.1.
10. application according to claim 6, which is characterized in that the temperature of hydroboration is room temperature, and the time is 20 points
Clock.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019200521A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of anilino lithium in catalyzing hydroboration of carbonyl compound and borane |
| WO2020073181A1 (en) * | 2018-10-08 | 2020-04-16 | 南通纺织丝绸产业技术研究院 | Application of o-methoxyaniline lithium for catalysing boron hydrogenation reaction of imine and borane |
| CN111747972A (en) * | 2020-06-16 | 2020-10-09 | 苏州大学 | Deprotonated beta-ketimine lithium compound and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749372A (en) * | 2016-12-07 | 2017-05-31 | 厦门大学 | A kind of preparation method of organic boronic ester compounds |
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2018
- 2018-04-16 CN CN201810336794.7A patent/CN108409770A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749372A (en) * | 2016-12-07 | 2017-05-31 | 厦门大学 | A kind of preparation method of organic boronic ester compounds |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019200521A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of anilino lithium in catalyzing hydroboration of carbonyl compound and borane |
| WO2020073181A1 (en) * | 2018-10-08 | 2020-04-16 | 南通纺织丝绸产业技术研究院 | Application of o-methoxyaniline lithium for catalysing boron hydrogenation reaction of imine and borane |
| CN111747972A (en) * | 2020-06-16 | 2020-10-09 | 苏州大学 | Deprotonated beta-ketimine lithium compound and preparation method thereof |
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