CN105669400A - Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation - Google Patents

Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation Download PDF

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CN105669400A
CN105669400A CN201610130897.9A CN201610130897A CN105669400A CN 105669400 A CN105669400 A CN 105669400A CN 201610130897 A CN201610130897 A CN 201610130897A CN 105669400 A CN105669400 A CN 105669400A
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iodide
sodium
reaction
potassium
phosphate
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韩维
钟延珍
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Nanjing Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • 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
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/068—Polyalkylene glycols
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for synthesizing a 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation. According to the method, carbon monoxide is taken as a carbonyl source, and an iodine catalyst is utilized for catalyzing carbonylation-alkylation domino reaction of benzyl chloride and an aryl boron reagent in medium polyethylene glycol in the presence of the iodine catalyst and alkali so as to directly prepare the 1,2,3-triaryl-1-acetone compound. In the method, noble metal catalysts and ligands are not used, and the reaction can be carried out under the normal pressure; and the method has the advantages that a substrate is wide in source, stable and low in cost, the catalyst is low in cost and easily available, little waste is produced, the application range is wide, the reaction selectivity is high, and the yield of the target product is high.

Description

A kind of method synthesizing 1,2,3-tri-aryl-1-acetonide without metal catalytic carbonylation benzyl chlorine
Technical field
The invention belongs to technical field of organic synthesis, it relates to a kind of method of catalyzed carbonylation benzyl chlorine, virtue borane reagent synthesis 1,2,3-tri-aryl-1-acetonide.
Background technology
1,2,3-tri-aryl-1-acetone compounds is the important organic synthesis intermediate of a class, is widely used in synthesizing three replacement alkene, the high value-added product such as indenes that four replacement alkene, many virtues replace and the different azoles heterocycle that Duo Fang replaces.
The carbonylation benzyl chlorine of palladium chtalyst and virtue borane reagent can synthesize 1,2-bis-virtue second ketone (Xiao-FengWu, HelfriedNeumann, MatthiasBeller, Adv.Synth.Catal.2011,353,788 792; Xiao-FengWu, HelfriedNeumann, MatthiasBeller, TetrahedronLetters, 2010,51,6146 6149.), and then the alkylated reaction carrying out benzyl chlorine in the effect of alkali can synthesize 1,2,3-tri-aryl-1-acetone. The method has simply, and selectivity is good, and the advantage of applied range. But, the method needs to use expensive and poisonous palladium metal and Phosphine ligands, and carbonylation step needs higher pressure, is required by conversion unit high, hinders the widespread use of the method greatly. In addition, the method needs two-step reaction, it is easy to causes a large amount of refuses to be formed, causes serious environmental problem.
Therefore, invent a kind of method not using metal and ligand catalyst to synthesize 1,2,3-tri-aryl-1-acetone compounds and there is important researching value and application prospect.
Summary of the invention
It is an object of the invention to provide a kind of without metal catalytic carbonylation benzyl chlorine, virtue borane reagent synthesis 1,2, the method of 3-tri-aryl-1-acetonide, described method is the method for the carbonylation-alkylation Domino reaction of a kind of benzyl chlorine, virtue borane reagent and carbon monoxide. The method original position forms 1,2-bis-virtue second ketone intermediate, it is not necessary to separation directly carries out alkylated reaction, can form 1,2,3-tri-aryl-1-acetone compounds. The method, without the need to noble metal catalyst and part, can be reacted under normal pressure, meanwhile, has substrate wide material sources, stable and cheap, catalyzer is cheap and easy to get, produce that refuse is few, applied widely, reaction preference height and the high advantage of target product yield.
The technical scheme of the present invention is as follows:
A kind of without metal catalytic carbonylation benzyl chlorine synthesis 1,2, the method of 3-tri-aryl-1-acetonide, it is characterised in that, in polyoxyethylene glycol solvent, under the effect of iodide catalyst and alkali, benzyl chlorine, virtue borane reagent and carbon monoxide generation carbonylation-alkylation Domino reaction, coupling forms 1,2,3-tri-aryl-1-acetonide, reaction expression is expressed as follows:
In formula, the phenyl ring of benzyl chlorine by adjacent, or contraposition R1Base replaces, it is possible to be monosubstituted or polysubstituted, R1Refer to and it is selected from arbitrarily hydrogen, the alkyl of C1～C12, alkenyl or alkynyl, C1～C12 alkoxyl group, C1～C12 fluorine substituted alkyl, fluorine substituted alkoxy, C1～C12 sulfydryl, the cycloalkyl of C3～C12, fluorine or chlorine;Virtue borane reagent refers to phenyl substituted boracic acid, boric acid ester or fluoroborate, its phenyl ring by adjacent, or contraposition R2Base replaces, it is possible to be monosubstituted or polysubstituted, R2Refer to and it is selected from arbitrarily hydrogen, the alkyl of C1～C12, alkenyl or alkynyl, C1～C12 alkoxyl group, C1～C12 fluorine substituted alkyl, fluorine substituted alkoxy, C1～C12 sulfydryl, the cycloalkyl of C3～C12, C1～C12 alkoxy carbonyl, aryl carbonyl, C1～C12 alkanoyloxy, cyano group, C1～C12 alkane alkylsulfonyl, sulfonic group, sulfonate group, phosphate-based, nitro, phenyl, fluorine or chlorine;
Described solvent is molecular-weight average is 200～20000 polyoxyethylene glycol. Preferred molecular-weight average is 400～1000 polyoxyethylene glycol, it is most preferred that solvent be PEG-4000.
Catalyzer of the present invention is inorganic iodine compound, forms catalyst system with solvent polyoxyethylene glycol and substitutes noble metal catalyst and ligand system, shows unexpectedly good catalytic activity and selectivity for target reaction. described iodide comprise sodium iodide, potassiumiodide, lithium iodide, cesium iodide, ammonium iodide, hydroiodic acid HI, iodine, tetrabutylammonium iodide, Tetramethylammonium iodide, tetraethyl ammonium iodide, zinc iodide, calcium iodide, trimethylammonium iodo sulfonic acid, tetrapropyl ammonium iodide, acetyl cholinesterase iodide, ethyltriphenylphosphiodide iodide phosphine, trimethylphenyl ammonium iodide, 1-butyl-3-methyl iodate imidazoles, bismuth iodide, nickelous iodide, copper(I) iodide, the sub-ketone of iodate, cobaltous iodide, methyl triphenyl iodate, 1-ethyl-3-methyl iodate imidazoles, 1-methyl-3-propyl group iodate imidazoles drone, 1, 2-dimethyl-3-propyl group iodate imidazoles etc. catalyzer most preferably can select the sodium iodide commonly used.
Described alkali is mineral alkali or organic bases. mineral alkali includes but not limited to Trilithium phosphate, hypophosphite monohydrate lithium, monometallic, phosphoric acid hydrogen two lithium, potassiumphosphate, hypophosphite monohydrate potassium, potassium primary phosphate, dipotassium hydrogen phosphate, sodium phosphate, sodium hydrogen phosphate, SODIUM PHOSPHATE, MONOBASIC, hypophosphite monohydrate sodium, Sodium Fluoride, Potassium monofluoride, cesium fluoride, Quilonum Retard, sodium carbonate, salt of wormwood, cesium carbonate, sodium acetate, potassium acetate, cesium acetate, sodium methylate, sodium ethylate, trimethyl carbinol lithium, lithium hydroxide, Sodium Propionate, potassium propionate, Sodium propanecarboxylate, potassium butyrate, trimethylacetic acid sodium, trimethylacetic acid potassium, organic bases includes but not limited to tetrabutyl ammonium fluoride, triethylamine, diisopropylethylamine, Tributylamine, 1,4-diazabicylo [2.2.2] octane or 1,5-diazabicylo [4.3.0]-5-in ninth of the ten Heavenly Stems alkene. and above-mentioned each alkali can combinationally use. alkali most preferably can select the composition of sodium phosphate and dipotassium hydrogen phosphate.
Described reaction is reacted at temperature 25-150 DEG C.
The pressure of described carbon monoxide 1～10 normal atmosphere. React under most preferably being normal pressure.
The inventive method adopts the carbonylation-alkylation Domino reaction of iodide catalysis benzyl chlorine, virtue borane reagent and carbon monoxide, the method original position forms 1,2-bis-virtue second ketone intermediate, alkylated reaction is directly carried out without the need to being separated, namely benzyl chlorine, virtue borane reagent and carbon monoxide coupling form target product 1,2,3-tri-aryl-1-acetonide. The method, without the need to noble metal catalyst and part, can be reacted under normal pressure, meanwhile, has substrate wide material sources, stable and cheap, catalyzer is cheap and easy to get, produce that refuse is few, applied widely, reaction preference height and the high advantage of target product yield.
Specifically, the method that the present invention synthesizes 1,2,3-tri-aryl-1-acetonide has following advantage:
1. catalyzer is iodide that are cheap, stable and that be easy to get.
2. raw material benzyl chlorine used is that in all benzyl halogen, price is the most cheap; Virtue borane reagent economy is easy to get, stable and nontoxic; It is good that reaction has functional group's consistency, produces the advantage that refuse is few and product rate is high.
3., without under transition-metal catalyst and part effect, under effectively achieving normal pressure, activate carbon monoxide, greatly reduce reaction cost and to the requirement of conversion unit, react safer and practical.
4. the medium used by reacting is eco-friendly green solvent polyoxyethylene glycol.
Embodiment
The present invention is further described below in conjunction with embodiment, but the scope not limited the present invention in any way.
Embodiment 1
Reaction flask and high-purity CO that stirrer is housed are connected by step 1, and vacuumize, fill carbon monoxide and repeat three times, make reaction system under carbon monoxide atmosphere.
Step 2 adds sodium iodide (0.075mmol) successively in reaction flask, sodium phosphate (2.0mmol), dipotassium hydrogen phosphate (0.1mmol), benzyl chlorine (1.0mmol or 1.5mmol), virtue boric acid (0.5mmol) and PEG-4000 (2.0g). Reaction mixture reacts at 100 DEG C, and extent of reaction is monitored by thin-layer chromatography or gas-chromatography.
After step 3 reaction terminates, cool to room temperature, with organic solvent extraction, merges organic phase, and concentrates and use column chromatography, namely obtain straight product.
Embodiment 2
Reaction flask and high-purity CO that stirrer is housed are connected by step 1, and vacuumize, fill carbon monoxide and repeat three times, make reaction system under carbon monoxide atmosphere.
Step 2 adds tetrabutylammonium iodide (0.075mmol) successively in reaction flask, sodium carbonate (2.0mmol), benzyl chlorine (1.0mmol or 1.5mmol), virtue potassium fluoborate (0.5mmol) and PEG-4000 (2.0g). Reaction mixture reacts at 100 DEG C, and extent of reaction is monitored by thin-layer chromatography or gas-chromatography.
After step 3 reaction terminates, cool to room temperature, with organic solvent extraction, merges organic phase, and concentrates and use column chromatography, namely obtain straight product.
Embodiment 3
Reaction flask and high-purity CO that stirrer is housed are connected by step 1, and vacuumize, fill carbon monoxide and repeat three times, make reaction system under carbon monoxide atmosphere.
Step 2 adds sodium iodide (0.075mmol) successively in reaction flask, sodium phosphate (2.0mmol), dipotassium hydrogen phosphate (0.1mmol), benzyl chlorine (1.0mmol or 1.5mmol), virtue boric acid (0.5mmol) and PEG-6000 (2.0g). Reaction mixture reacts at 100 DEG C, and extent of reaction is monitored by thin-layer chromatography or gas-chromatography.
After step 3 reaction terminates, cool to room temperature, with organic solvent extraction, merges organic phase, and concentrates and use column chromatography, namely obtain straight product.
Embodiment 4～15
1 is synthesized without metal catalytic carbonylation benzyl chlorine, 2,3-tri-aryl-1-acetonide, taking polyoxyethylene glycol solvent and iodide as catalyst system, under alkali effect, benzyl chlorine, virtue borane reagent and carbon monoxide generation carbonylation-alkylation Domino reaction, coupling forms 1,2,3-tri-aryl-1-acetonide, reaction formula is expressed as follows:
In prepared by particular compound, benzyl chlorine is as shown in table 1 with the substituting group in virtue borane reagent; Reaction solvent is molecular-weight average 400～1000 polyoxyethylene glycol, catalyst iodine compound be selected from sodium iodide, potassiumiodide, tetrabutylammonium iodide, calcium iodide, trimethylammonium iodo sulfonic acid, 1-butyl-3-methyl iodate imidazoles, iodate sub-ketone, cobaltous iodide one or both;Alkali be selected from sodium phosphate, sodium hydrogen phosphate, dipotassium hydrogen phosphate, Quilonum Retard, sodium carbonate, sodium methylate, trimethyl carbinol lithium, tetrabutyl ammonium fluoride, triethylamine one or both;
React at temperature 25-150 DEG C, the pressure of carbon monoxide 1～10 normal atmosphere.
Concrete steps are similar to the method for embodiment 1～3, and reaction result is in table 1:
Table 1 synthesizes 1,2,3-tri-aryl-1-acetonide reaction result without metal catalytic carbonylation benzyl chlorine
[a] separation yield.

Claims (7)

1. one kind is synthesized 1 without metal catalytic carbonylation benzyl chlorine, 2, the method of 3-tri-aryl-1-acetonide, it is characterised in that, in polyoxyethylene glycol solvent, under the effect of iodide catalyst and alkali, benzyl chlorine, virtue borane reagent and carbon monoxide generation carbonylation-alkylation Domino reaction, coupling forms 1,2,3-tri-aryl-1-acetonide, reaction expression is expressed as follows:
Substituent R in formula, on the phenyl ring of benzyl chlorine1For monosubstituted or polysubstituted, R1Refer to and it is selected from arbitrarily hydrogen, the alkyl of C1～C12, alkenyl or alkynyl, C1～C12 alkoxyl group, C1～C12 fluorine substituted alkyl, fluorine substituted alkoxy, C1～C12 sulfydryl, the cycloalkyl of C3～C12, fluorine or chlorine;
Virtue borane reagent refers to phenyl substituted boracic acid, boric acid ester or fluoroborate, the substituent R on its phenyl ring2For monosubstituted or polysubstituted, R2Refer to and it is selected from arbitrarily hydrogen, the alkyl of C1～C12, alkenyl or alkynyl, C1～C12 alkoxyl group; C1～C12 fluorine substituted alkyl, fluorine substituted alkoxy, C1～C12 sulfydryl, the cycloalkyl of C3～C12; C1～C12 alkoxy carbonyl, aryl carbonyl, C1～C12 alkanoyloxy; cyano group, C1～C12 alkane alkylsulfonyl, sulfonic group; sulfonate group, phosphate-based, nitro; phenyl, fluorine or chlorine.
2. synthetic method according to claim 1, it is characterised in that, described solvent is molecular-weight average is 200～20000 polyoxyethylene glycol.
3. synthetic method according to claim 2, it is characterised in that, described solvent is molecular-weight average is 400～1000 polyoxyethylene glycol.
4. synthetic method according to claim 1, it is characterized in that, described iodide are selected from sodium iodide, potassiumiodide, lithium iodide, cesium iodide, ammonium iodide, hydroiodic acid HI, iodine, tetrabutylammonium iodide, Tetramethylammonium iodide, tetraethyl ammonium iodide, zinc iodide, calcium iodide, trimethylammonium iodo sulfonic acid, tetrapropyl ammonium iodide, acetyl cholinesterase iodide, ethyltriphenylphosphiodide iodide phosphine, trimethylphenyl ammonium iodide, 1-butyl-3-methyl iodate imidazoles, bismuth iodide, nickelous iodide, copper(I) iodide, the sub-ketone of iodate, cobaltous iodide, methyl triphenyl iodate, 1-ethyl-3-methyl iodate imidazoles, 1-methyl-3-propyl group iodate imidazoles drone or 1, 2-dimethyl-3-propyl group iodate imidazoles.
5. synthetic method according to claim 1, it is characterized in that, described alkali is mineral alkali or organic bases, mineral alkali is selected from Trilithium phosphate, hypophosphite monohydrate lithium, monometallic, phosphoric acid hydrogen two lithium, potassiumphosphate, hypophosphite monohydrate potassium, potassium primary phosphate, dipotassium hydrogen phosphate, sodium phosphate, sodium hydrogen phosphate, SODIUM PHOSPHATE, MONOBASIC, hypophosphite monohydrate sodium, Sodium Fluoride, Potassium monofluoride, cesium fluoride, Quilonum Retard, sodium carbonate, salt of wormwood, cesium carbonate, sodium acetate, potassium acetate, cesium acetate, sodium methylate, sodium ethylate, trimethyl carbinol lithium, lithium hydroxide, Sodium Propionate, potassium propionate, Sodium propanecarboxylate, potassium butyrate, one or more in trimethylacetic acid sodium or trimethylacetic acid potassium, organic bases be selected from tetrabutyl ammonium fluoride, triethylamine, diisopropylethylamine, Tributylamine, 1,4-diazabicylo [2.2.2] octane or 1,5-diazabicylo [4.3.0]-5-in ninth of the ten Heavenly Stems alkene one or more.
6. synthetic method according to claim 1, it is characterised in that, the pressure of described carbon monoxide is 1～10 normal atmosphere.
7. synthetic method according to claim 1, it is characterised in that, described temperature of reaction is 25-150 DEG C.
CN201610130897.9A 2016-03-08 2016-03-08 Method for synthesizing 1,2,3-triaryl-1-acetone compound from benzyl chloride through non-metal-catalyzed carbonylation Pending CN105669400A (en)

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CN113264844A (en) * 2021-06-01 2021-08-17 宿州学院 Method for preparing aryl amide compound by catalyzing carbonylation of aryl tertiary amine through metal-free catalytic system

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113264844A (en) * 2021-06-01 2021-08-17 宿州学院 Method for preparing aryl amide compound by catalyzing carbonylation of aryl tertiary amine through metal-free catalytic system
CN113264844B (en) * 2021-06-01 2023-05-02 宿州学院 Method for preparing aryl amide compound by catalyzing carbonylation of aryl tertiary amine without metal catalytic system

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