CN110256474B - Application of trisilamine rare earth complex in catalyzing reaction of carbonate and borane - Google Patents

Application of trisilamine rare earth complex in catalyzing reaction of carbonate and borane Download PDF

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CN110256474B
CN110256474B CN201910647023.4A CN201910647023A CN110256474B CN 110256474 B CN110256474 B CN 110256474B CN 201910647023 A CN201910647023 A CN 201910647023A CN 110256474 B CN110256474 B CN 110256474B
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carbonate
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rare earth
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earth complex
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薛明强
徐晓娟
康子晗
陈素芳
刘倩倩
蔡玲霞
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    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/37—Lanthanum
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/38—Lanthanides other than lanthanum

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Abstract

The invention discloses an application of a trisilamine rare earth complex in catalyzing the reaction of carbonic ester and borane, which comprises the following steps of reacting the borane and the carbonic ester in the presence of the trisilamine rare earth complex in a nitrogen atmosphere to obtain boric ester. The rare earth complex is used for catalyzing the hydroboration reaction of the carbonic ester and the pinacol borane for the first time, so that a novel efficient catalyst for catalyzing the hydroboration reaction is developed, the structure is simple, the synthesis is easy, the application of the trisilamine rare earth complex is expanded, and the method for synthesizing the carbonic ester and the pinacol borane is enriched.

Description

Application of trisilamine rare earth complex in catalyzing reaction of carbonate and borane
Technical Field
The invention relates to the field of application of rare earth metal organic complexes, in particular to application of trisilamino rare earth complexes in catalyzing hydroboration reaction of carbonic ester and borane.
Background
The organoborates may be regarded as orthoboric acid B (OH)3Wherein hydrogen is substituted by an organic group, and a metaborate (ROBO)3. The borate compound has wide application range, is a main raw material for synthesizing boron-containing compounds, and is one of important applications. In addition, the borate compound can be used as an antirust agent of a cleaning agent, an antiseptic, a polymer additive, an antiwear additive, automobile brake fluid, a gasoline additive and a flame retardant, and can also be used as a lubricating oil additive and the like.
Since the pioneering research on borane by Stock et al in 1912, the electron-deficient characteristics and the nature of chemical bonds of borane have attracted attention, and the research on borane has become an important research field in the chemical science. Alkyl borate has recently become a hot research field of organoboron compounds, and has been widely researched and applied as hydrogen storage materials, as reducing agents in organic reactions, chiral catalytic agents, and the like. The existing catalytic system uses transition metal Mn complex as catalyst, NaOtBu as co-catalystThe agent needs higher temperature to realize the efficient reaction.
Disclosure of Invention
The invention aims to provide the application of the trisilamine rare earth complex, which can catalyze carbonate and pinacol borane to prepare borate, and has high catalytic activity, low catalyst consumption and good substrate application range.
In order to achieve the purpose, the invention adopts the technical scheme that: the application of trisilamide rare earth complex in catalyzing the reaction of carbonic ester and borane; the chemical structural formula of the trisilamide rare earth complex is as follows:
Figure 228481DEST_PATH_IMAGE001
a method for preparing borate ester comprises the following steps of reacting borane with carbonate ester in the presence of trisilamide rare earth complex in a nitrogen atmosphere to obtain the borate ester.
The molecular formula of the trisilamine rare earth complex can be expressed as follows: RE [ N (SiMe)3)2]3RE represents rare earth metal selected from one of lanthanum, yttrium, neodymium, ytterbium and samarium in lanthanide.
In the technical scheme, the borane is pinacol borane; the carbonate is ethylene carbonate, propylene carbonate, styrene carbonate, chlorostyrene carbonate, tert-butylstyrene carbonate, dimethyl carbonate, dibenzyl carbonate, trimethylene carbonate, etc.; or the chemical structural formula of the carbonate is as follows:
Figure 348884DEST_PATH_IMAGE002
in the technical scheme, the dosage of the trisilicamine rare earth complex is 0.5 percent of the molar weight of the carbonate; the molar ratio of the borane to the carbonate is 3.3: 1.
In the above technical scheme, the reaction temperature is room temperature.
The invention discloses a method for preparing boric acid ester by using trisilamine rare earth complex as a catalyst, which comprises the following steps:
all raw materials are subjected to anhydrous and oxygen-free treatment, and a catalyst, borane and carbonate are mixed in a nitrogen atmosphere; then reacting for 6h at room temperature, and then contacting with air to terminate the reaction, thus obtaining the different substituted boric acid ester.
The above technical solution can be expressed as follows:
Figure 394201DEST_PATH_IMAGE003
due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
1. the rare earth complex is used for catalyzing the hydroboration reaction of the carbonic ester and the pinacol borane for the first time, so that a novel efficient catalyst for catalyzing the hydroboration reaction is developed, the structure is simple, the synthesis is easy, the application of the trisilamine rare earth complex is expanded, and the method for synthesizing the carbonic ester and the pinacol borane is enriched.
2. The trisilamine rare earth complex disclosed by the invention can catalyze the hydroboration reaction of carbonic ester and borane with high activity at room temperature, the dosage of the catalyst is only 0.5% of the molar weight of the carbonic ester, the reaction yield can reach more than 99%, and compared with the existing catalytic system, the dosage of the catalyst is reduced, and the yield is improved.
The trisilamine rare earth complex disclosed by the invention has a wide application range to substrates, is suitable for carbonates with different substituent positions and different electronic effects, and provides more choices for industrial synthesis of borate; and the reaction process is simple and controllable, the yield is high, the product is easy to post-treat, and the method is suitable for industrial production.
Detailed Description
The invention is further described below with reference to the following examples:
EXAMPLE one La [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing ethylene carbonate and pinacol borane
Under nitrogen atmosphere, is passed throughAdding catalyst La [ N (SiMe) into the reaction bottle after dehydration and deoxidation treatment3)2]3 (3.1 mg, 0.005mmol), ethylene carbonate (66.6. mu.L, 1 mmol) was added using a pipette, then pinacolborane (435.9. mu.L, 3 mmol) was added using a pipette, the reaction was terminated by exposure to air after 6 hours at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield by H spectrum is 70%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ 3.94 (s, 4H, CH2), 3.60 (s, 3H, CH3OBpin), 1.25 (d, 40H, CH3)。
EXAMPLE two Yb [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing ethylene carbonate and pinacol borane
Adding catalyst Yb [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.3 mg, 0.005mmol), ethylene carbonate (66.6. mu.L, 1 mmol) was added using a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added using a pipette, the reaction was terminated by exposure to air after 6 hours at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 30%. The nuclear magnetic data of the product are the same as in example one.
Example three: nd [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing ethylene carbonate and pinacol borane
Adding a catalyst Nd [ N (SiMe) into a reaction bottle subjected to dehydration and deoxidation treatment in a nitrogen atmosphere3)2]3 (3.2 mg, 0.005mmol), ethylene carbonate (66.6. mu.L, 1 mmol) was added using a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added using a pipette, the reaction was terminated by exposure to air after 6 hours at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 94%. The nuclear magnetic data of the product are the same as in example one.
Example four: la [ N (SiMe)3)2]3Catalysis of ethylene carbonateAnd pinacolborane Synthesis of Borate esters
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), ethylene carbonate (66.6. mu.L, 1 mmol) was added using a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added using a pipette, the reaction was terminated by exposure to air after 6 hours at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. The nuclear magnetic data of the product are the same as in example one.
Example five: la [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing propylene carbonate and pinacol borane
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), propylene carbonate (84.8. mu.L, 1 mmol) was added with a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added with a pipette, after reacting for 6 hours at room temperature, the reaction was terminated by contacting with air, one drop was pipetted into a nuclear magnetic tube, CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 97%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ4.30-4.26 (m, 1H, CH), 3.75 (d, 2H, CH2), 3.60 (s, 3H, CH3OBpin), 1.24 (s, 40H, OBpin), 1.17 (d, 3H, CH3)。
example six: la [ N (SiMe)3)2]3Method for synthesizing boric acid ester by catalyzing phenylethylene carbonate and pinacol borane
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), styrene carbonate (164.2 mg, 1 mmol) was added, then pinacolborane (478.8. mu.L, 3.3 mmol) was added with a pipette, after reacting for 6 hours at room temperature, the reaction was terminated by contacting with air, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ 7.31-7.16 (m, 5H, ArCH), 5.17-5.14 (m, 1H, CH), 3.90-3.80 (m, 2H, CH2), 3.51 (s, 3H, CH3OBpin), 1.15 (d, 40H, OBpin)。
EXAMPLE seven La [ N (SiMe)3)2]3Boric acid ester synthesized by catalyzing chloroethylene carbonate and pinacol borane
The chemical structural formula of the chlorostyrene carbonate is as follows:
Figure 117306DEST_PATH_IMAGE004
adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), chlorostyrene carbonate (198.6 mg, 1 mmol) was added, followed by the addition of pinacolborane (478.8. mu.L, 3.3 mmol) with a pipette, reaction was terminated by exposure to air after 6 hours at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 94%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ 7.28-7.20 (m, 4H, ArCH), 5.12-5.09 (m, 1H, CH), 3.87-3.80 (m, 2H, CH2), 3.55 (s, 3H, CH3OBpin), 1.21-1.15 (m, 40H, OBpin)。
EXAMPLE eight La [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing tert-butyl styrene carbonate and pinacol borane
The chemical structural formula of tert-butyl styrene carbonate is as follows:
Figure 197257DEST_PATH_IMAGE005
adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), tert-butylstyrene carbonate (220.27 mg, 1 mmol) was added followed by pinacolborole addition with a pipetteAlkane (478.8 mu L, 3.3 mmol), reacting at room temperature for 6h, terminating the reaction by contacting with air, dropping one drop by pipette into a nuclear magnetic tube, adding CDCl3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ 7.28-7.23 (m, 4H, ArCH), 5.16-5.12 (m, 1H, CH), 3.90-3.80 (m, 2H, CH2), 3.52 (s, 3H, CH3OBpin), 1.23 (s, 9H, C(CH3)3), 1.18-1.13 (m, 40H, OBpin)。
EXAMPLE nine La [ N (SiMe)3)2]3Catalytic synthesis of boronic esters from trimethylene carbonate and pinacol borane
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), trimethylene carbonate (102.09 mg, 1 mmol) was added, followed by the addition of pinacolborane (478.8. mu.L, 3.3 mmol) using a pipette, reacted at room temperature for 6 hours, and then one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ3.95-3.92 (m, 4H, CH2), 3.60 (s, 3H, CH3OBpin), 1.87-1.80 (q, 4H, CH2), 1.26-1.24 (m, 40H, OBpin)。
EXAMPLE ten La [ N (SiMe)3)2]3Catalytic synthesis of boronic esters from carbonate and pinacol borane
The chemical structure of the carbonate is as follows:
Figure 222982DEST_PATH_IMAGE002
adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), carbonate (157.6. mu.L, 1 mmol) was added using a pipette, followed by pinacolborane (478.8. mu.L, 3.3 mmol) and reacted at room temperature for 6 hours, followed by pipetting one drop into a nuclear magnetic tubeIn (1), adding CDCl3Preparing a solution. Is calculated by1The yield of the H spectrum is 95%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ3.61 (d, 4H, CH2), 3.55 (s, 3H, CH3OBpin), 1.21-1.19 (m, 44H, OBpin & (CH2)2), 0.85-0.78 (m, 6H, CH3)。
EXAMPLE eleven La [ N (SiMe)3)2]3Catalytic synthesis of boric acid ester from dibenzyl carbonate and pinacol borane
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), dibenzyl carbonate (210.4. mu.L, 1 mmol) was added using a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added using a pipette, and after 6 hours of reaction at room temperature, the reaction was terminated by exposure to air, and a drop of air was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ7.35-7.23 (m, 10H, ArCH), 4.92 (s, 4H, CH2), 3.60 (s, 3H, CH3OBpin), 1.25 (d, 40H, OBpin)。
example twelve Cp3Nd-catalyzed synthesis of boric acid ester from dimethyl carbonate and pinacol borane
Adding a catalyst Cp into a reaction bottle subjected to dehydration and deoxidation treatment in a nitrogen atmosphere3Nd (1.7 mg, 0.005mmol), dimethyl carbonate (84.2. mu.L, 1 mmol) was added with a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added with a pipette, after 6 hours of reaction at room temperature, the reaction was terminated by exposure to air, a drop of a pipette was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. The starting material was calculated to be unreacted.
Example thirteen Cp3Nd-catalyzed synthesis of boric acid ester from ethylene carbonate and pinacol borane
Adding a catalyst Cp into a reaction bottle subjected to dehydration and deoxidation treatment in a nitrogen atmosphere3Nd (1.7 mg, 0.005mmol), ethylene carbonate (66.6. mu.L, 1 mmol) was added with a pipette,then adding pinacolborane (478.8 mu L, 3.3 mmol) by using a liquid transfer gun, reacting at room temperature for 6h, stopping the reaction by contacting with air, sucking one drop by using a dropper into a nuclear magnetic tube, and adding CDCl3Preparing a solution. The starting material was calculated to be unreacted.
The rare earth metallocene catalyst can not catalyze the hydroboration of carbonic ester under the current conditions.
EXAMPLE fourteen La [ N (SiMe)3)2]3Synthesis of boric acid ester by catalyzing dimethyl carbonate and pinacol borane
Adding catalyst La [ N (SiMe) into the reaction flask after dehydration and deoxidation treatment in nitrogen atmosphere3)2]3 (3.1 mg, 0.005mmol), dimethyl carbonate (84.2. mu.L, 1 mmol) was added using a pipette, then pinacolborane (478.8. mu.L, 3.3 mmol) was added using a pipette, the reaction was terminated by exposure to air after 6 hours of reaction at room temperature, one drop was pipetted into a nuclear magnetic tube, and CDCl was added3Preparing a solution. Is calculated by1The yield of the H spectrum is 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3) δ 3.53 (s, 9H, CH3OBpin), 1.18 (s, 40H, OBpin)。
the trisilamine rare earth metal organic complex has the advantages of easiness in synthesis, low cost and the like, has Ln-N bonds, uses a lower catalyst dosage as a catalyst, is mild in reaction conditions, and can efficiently catalyze the hydroboration of carbonic ester to generate alkyl borate under the condition of no solvent.

Claims (3)

1. The application of trisilamide rare earth complex in catalyzing the reaction of carbonic ester and borane; the chemical structural formula of the trisilamide rare earth complex is as follows:
Figure DEST_PATH_IMAGE001
wherein RE represents rare earth metal lanthanum;
the borane is pinacol borane; the carbonate is ethylene carbonate, propylene carbonate, styrene carbonate, chlorostyrene carbonate, tert-butyl styrene carbonate, dibenzyl carbonate and trimethylene carbonate; or the chemical structural formula of the carbonate is as follows:
Figure DEST_PATH_IMAGE002
。
2. the use according to claim 1, wherein the trisilicamine rare earth complex is used in an amount of 0.5% by mole based on the carbonate; the molar ratio of the borane to the carbonate is 3.3: 1.
3. Use according to claim 1, wherein the reaction is carried out at room temperature for a period of 6 hours.
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