CN108409771A - The method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium - Google Patents
The method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium Download PDFInfo
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- CN108409771A CN108409771A CN201810336917.7A CN201810336917A CN108409771A CN 108409771 A CN108409771 A CN 108409771A CN 201810336917 A CN201810336917 A CN 201810336917A CN 108409771 A CN108409771 A CN 108409771A
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- aldehyde
- hydroboration
- methyl
- borine
- benzene amido
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- 238000006197 hydroboration reaction Methods 0.000 title claims abstract description 36
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 26
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 125000003368 amide group Chemical group 0.000 title claims abstract description 22
- 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 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910000085 borane Inorganic materials 0.000 claims abstract description 26
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 150000002192 fatty aldehydes Chemical group 0.000 claims abstract description 11
- 230000018044 dehydration Effects 0.000 claims abstract description 8
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 8
- 238000012545 processing Methods 0.000 claims abstract description 8
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical group CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 12
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 claims description 5
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical group O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims description 3
- -1 boric acid ester compound Chemical class 0.000 abstract description 7
- 239000004327 boric acid Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 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 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XVTIGBVLQZAFQP-UHFFFAOYSA-N C=O.C1(CCCCC1)C1=CC=CC=C1 Chemical compound C=O.C1(CCCCC1)C1=CC=CC=C1 XVTIGBVLQZAFQP-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910010277 boron hydride Inorganic materials 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
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- IFOBAKIQHNOSRE-UHFFFAOYSA-N lithium;phenylazanide Chemical compound [Li+].[NH-]C1=CC=CC=C1 IFOBAKIQHNOSRE-UHFFFAOYSA-N 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses carry out the method that hydroboration prepares borate based on o-methyl-benzene amido lithium；Under anhydrous and oxygen-free environment, in atmosphere of inert gases, borine is added in the reaction bulb by dehydration and deoxidation processing, then catalyst o-methyl-benzene amido lithium is added, is uniformly mixed, adds aldehyde, hydroboration is carried out, is exposed in air and terminates reaction, obtain product borate；The aldehyde is selected from fatty aldehyde.Catalyst disclosed by the invention has preferable universality for different structure fatty aldehyde, and the boric acid ester compound to obtain different substituents structure provides more selections.
Description
Technical field
The application of o-methyl-benzene amido lithium of the present invention, and in particular to hydroboration is carried out based on o-methyl-benzene amido lithium
The method that reaction prepares borate.
Technical background
Since the hydroboration that Brown in 1956 et al. has found boron hydride catalyzed alkene, for unsaturated bond
Hydroboration has become a kind of very effective means for preparing various organic synthesis intermediates, for unsaturated bond
Hydroboration research all has great importance for modern industry and Synthetic Organic Chemistry, so as to cause research work
Person widely pays close attention to.
Various catalyst have been used for the hydroboration of aldehyde, 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, develop the catalysis of the hydroboration of efficient catalytic aldehyde under new temperate condition
System is particularly urgent.
Invention content
The goal of the invention of the present invention is to provide the method for carrying out hydroboration based on o-methyl-benzene amido lithium, i.e., with adjacent first
Base anilino- lithium is the application that effective catalyst is catalyzed that hydroboration occurs with borine for aldehyde；The o-methyl-benzene amido lithiumation
Formula is：2-Me-PhNHLi, chemical structural formula are as follows：
To achieve the above object of the invention, the technical solution adopted by the present invention is：
The method that hydroboration prepares borate is carried out based on o-methyl-benzene amido 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 o-methyl-benzene amido lithium, be uniformly mixed, add aldehyde, carry out hydroboration, is exposed in air and terminates reaction,
Obtain product borate；The aldehyde is selected from fatty aldehyde.
The present invention further discloses o-methyl-benzene amido lithium in catalysis aldehyde and the application in borine hydroboration；Institute
It states aldehyde and is selected from fatty aldehyde.
The invention also discloses the methods of the 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 catalyst o-methyl-benzene amido lithium, be uniformly mixed, add aldehyde, carries out hydroboration.
In above-mentioned technical proposal, the fatty aldehyde hexahydrobenzaldehyde, propionic aldehyde, n-Heptaldehyde；
The borine is selected from pinacol borine.
In above-mentioned technical proposal, the catalyst amount is the 0.1% of aldehyde mole, and the molar ratio of aldehyde and borine is 1:
1.1。
In above-mentioned technical proposal, the temperature of hydroboration is room temperature, and the reaction time is 10 minutes.
Above-mentioned technical proposal can indicate as follows：
R1Come from raw material aldehyde.
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.
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 o-methyl-benzene amido lithium, which extremely can efficiently be catalyzed fatty aldehyde and borine, occurs hydroboration,
New scheme is provided to prepare borate with borine generation hydroboration using carbonyls.
2. the catalytic activity height that hydroboration occurs with borine for o-methyl-benzene amido lithium catalysis aldehyde disclosed by the invention (is urged
Agent dosage is only 0.1 %), reaction condition is mild (room temperature), and the reaction time is short (10min), and reaction yield is high, and reaction is simple
Controllably, post-processing is simple, and reaction uses solvent-free system, reduces the pollution to environment.
3. catalyst disclosed by the invention has preferable universality for different structure fatty aldehyde, to obtain different substitutions
The boric acid ester compound of based structures provides more selections.
Specific implementation mode
The present invention is described further with reference to embodiment：
Embodiment one：O-methyl-benzene amido lithium is catalyzed cyclohexyl benzene formaldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul o-methyl-benzene amido lithiums are added of argon gas protection is molten
Liquid (0.05M) (0.1 mol% dosages, similarly hereinafter), then with syringe be added 0.1596 mL borines, be uniformly mixed, then with inject
0.095 mL2- pyridine carboxaldehydes are added in device, and mixture is stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, is subtracted later
Pressure removes a small amount of tetrahydrofuran and excessive borine to get to corresponding pinacol borate C6H5COCH2OB(OC(CH3)2C
(CH3)2O)。1H NMR (400 MHz, CDCl3) δ 8.61 (d, J = 5.4 Hz, 1H, Ar-H), 7.91 (t, J
= 7.7 Hz, 1H, Ar-H), 7.49-7.41 (m, 2H, Ar-H), 5.10 (s, 2H, OCH2), 1.32 (s,
12H, CH3)。 13C NMR (101 MHz, CDCl3) δ 159.82 (Ar-C), 143.72 (Ar-C), 139.56
(Ar-C), 123.39 (Ar-C), 120.09 (Ar-C), 81.04 (OC), 66.47 (OCH2), 25.47 (CH3)。
Embodiment two：O-methyl-benzene amido lithium is catalyzed propionic aldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul o-methyl-benzene amido lithiums are added of argon gas protection is molten
Then 0.1596 mL borines are added with syringe in liquid (0.05M) (0.1 mol% dosages), are uniformly mixed, then be added with syringe
0.072 mL propionic aldehyde, mixture are stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, is removed under reduced pressure later a small amount of
Tetrahydrofuran and excessive borine are to get to corresponding pinacol borate CH3CH2COCH2OB(OC(CH3)2C(CH3)2O)。1H
NMR (400 MHz, CDCl3) δ 3.80 (t, J = 6.6 Hz, 2H, OCH2), 1.63-1.54 (m, 2H, CH2),
1.25 (s, 12H, CH3), 0.91 (t, J = 7.4 Hz, 3H, CH3)。 13C NMR (101 MHz, CDCl3) δ
82.04 (OC), 66.02 (OCH2), 24.14 (CH3CH2), 24.05 (CH3), 9.55 (CH2CH3)。
O-methyl-benzene amido lithium is replaced with to the amido lithium compound of formula I, it is virtually impossible to obtain product, yield is less than 6%.
Embodiment three：O-methyl-benzene amido lithium is catalyzed n-Heptaldehyde and pinacol borine hydroboration
In the reaction bulb by dehydration and deoxidation processing, the lower tetrahydrofuran that 20ul o-methyl-benzene amido lithiums are added of argon gas protection is molten
Then 0.1596 mL borines are added with syringe in liquid (0.05M) (0.1 mol% dosages), are uniformly mixed, then be added with syringe
0.1392 mL n-Heptaldehydes, mixture are stirred at room temperature, and after reacting 10 min, nuclear-magnetism yield is 99%, are removed under reduced pressure later few
The tetrahydrofuran of amount and excessive borine are to get to corresponding pinacol borate C6H13COCH2OB(OC(CH3)2C(CH3)2O)
。1H NMR (400 MHz, CDCl3) δ 3.82 (t, J = 8 Hz, 2H, OCH2), 1.52-1.58 (m, 2H,
CH2), 1.27-1.34 (m, 8H, CH2), 1.24 (s, 12H, CH3), 0.87 (t, J = 8 Hz, 3H, CH3)。13C NMR (100 MHz, CDCl3) δ 82.02 (OC), 64.40 (OCH2), 31.29 (CH2), 30.92 (CH2),
28.44 (CH2), 25.02 (CH2), 24.00 (CH3), 22.05 (CH2), 13.51 (CH3)。
Present invention firstly discovers that o-methyl-benzene amido lithium can be catalyzed the hydroboration of aldehyde with high catalytic activity, and
And there is very wide substrate usage range.Cheap catalyst and lower catalyst amount, mild catalysis item
Part provides possibility for industrial applications.
Claims (10)
1. carrying out the method that hydroboration prepares borate based on o-methyl-benzene amido lithium, include 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 o-methyl-benzene amido lithium, be uniformly mixed, add aldehyde, carries out hydroboration；It is then exposed to terminate in air
Reaction, obtains borate；The aldehyde is selected from fatty aldehyde.
2. the method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium according to claim 1, it is special
Sign is that the fatty aldehyde is selected from hexahydrobenzaldehyde, propionic aldehyde, n-Heptaldehyde；The borine is selected from pinacol borine.
3. the method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium according to claim 1, it is special
Sign is, the dosage of the catalyst is 0.1 % of aldehyde mole, and the molar ratio of aldehyde and borine is 1: 1.1.
4. the method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium according to claim 1, it is special
Sign is that the temperature of reaction is room temperature.
5. the method that hydroboration prepares borate is carried out based on o-methyl-benzene amido lithium according to claim 1, it is special
Sign is that the time of the reaction is 10min.
6. o-methyl-benzene amido lithium is in catalysis aldehyde and the application in borine hydroboration；The aldehyde is fatty aldehyde.
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 o-methyl-benzene amido lithium, be uniformly mixed, add aldehyde, carries out hydroboration.
8. application according to claim 6, which is characterized in that the fatty aldehyde is selected from hexahydrobenzaldehyde, propionic aldehyde, positive heptan
Aldehyde；The borine is selected from pinacol borine.
9. application according to claim 6, which is characterized in that the dosage of the catalyst is 0.1 % of aldehyde mole, aldehyde
Molar ratio with borine is 1: 1.1.
10. application according to claim 6, which is characterized in that the temperature of the hydroboration is room temperature, and the time is
10min。
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109289914A (en) * | 2018-09-27 | 2019-02-01 | 苏州大学张家港工业技术研究院 | Application of the o-methyl-benzene amido lithium in catalysis imines and borine hydroboration |
| 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 |
| WO2019200522A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of o-methylanilino 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 |
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 |
-
2018
- 2018-04-16 CN CN201810336917.7A patent/CN108409771A/en active Pending
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 (5)
| 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 |
| WO2019200522A1 (en) * | 2018-04-17 | 2019-10-24 | 南通纺织丝绸产业技术研究院 | Application of o-methylanilino lithium in catalyzing hydroboration of carbonyl compound and borane |
| CN109289914A (en) * | 2018-09-27 | 2019-02-01 | 苏州大学张家港工业技术研究院 | Application of the o-methyl-benzene amido lithium in catalysis imines and borine hydroboration |
| CN109289914B (en) * | 2018-09-27 | 2020-04-17 | 苏州大学张家港工业技术研究院 | Application of o-methyl aniline lithium in catalyzing imine and borane hydroboration reaction |
| 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 |
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Application publication date: 20180817 |