CN108191612A - The preparation method and application of compound aryl trifluoromethyl - Google Patents
The preparation method and application of compound aryl trifluoromethyl Download PDFInfo
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- CN108191612A CN108191612A CN201711489777.9A CN201711489777A CN108191612A CN 108191612 A CN108191612 A CN 108191612A CN 201711489777 A CN201711489777 A CN 201711489777A CN 108191612 A CN108191612 A CN 108191612A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
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Abstract
The present invention discloses a kind of preparation method and application of compound aryl trifluoromethyl.The preparation method includes：Under illumination and alkaline condition, compound A and trifluoromethyl reagent is made to react in the organic solvent system containing catalyst, obtain compound aryl trifluoromethyl；The structural formula of the compound A is as follows：A、
Description
Technical field
The invention belongs to the synthesis technical fields of trifluoromethyl compound, particularly relate to a kind of aryl trifluoromethyl
The preparation method and application of compound.
Background technology
Fragrant trifluoromethyl compound is a kind of important organic fluorocompound, can be widely applied to pesticide, medicine, function material
In material and dyestuff.Conventional construction CF3Method include being catalyzed using transition metal copper or palladium compound, using specific
Functional group is as activated group.Although making great progress in recent years, following defect is still had：Copper or palladium exist
There is residual in pharmaceutical synthesis；It needs using ligand and excessive and expensive trifluoromethyl reagent；It needs to provide function dough for oneself
Precursor compound (such as halogenated aryl hydrocarbon, aryl boric acid).
Therefore, we are special in the prior art to overcome there is an urgent need to a kind of method of new compound aryl trifluoromethyl
The defects of being the above.
Invention content
It is an object of the invention to overcome the above-mentioned deficiency of the prior art, a kind of compound aryl trifluoromethyl is provided
Preparation method, to solve that existing compound aryl trifluoromethyl preparation condition is harsh, process is complicated and product has the catalyst residual
The technical problems such as stay.
Further, the present invention also provides the applications of the compound aryl trifluoromethyl.
In order to achieve the above-mentioned object of the invention, the preparation method of compound aryl trifluoromethyl, including at least following steps：
Under illumination condition and alkaline condition, make compound A and trifluoromethyl reagent in the organic solvent containing catalyst
It reacts in system, obtains compound aryl trifluoromethyl；
The structural formula of wherein described compound A is as follows：
The R in the Compound A structure formula is alkyl, halogen, nitro, alkoxy, hydroxyl, one kind in carboxyl or
It is two or more.
As another aspect of the present invention, the present invention provides the preparation sides of the invention described above compound aryl trifluoromethyl
The application of compound aryl trifluoromethyl prepared by method in the preparation of medicine, pesticide and functional material.
Compared with prior art, the preparation method of compound aryl trifluoromethyl of the present invention, reaction condition is simple, and reaction is former
The effect of material only light requirement photograph, alkaline condition and catalyst, you can obtain compound aryl trifluoromethyl, preparation process need not match
Body, without precursor compound, product is remained without catalyst.
Preparation method just because of compound aryl trifluoromethyl of the present invention has above-mentioned progressive, therefore, can be wide
The general preparation for medicine, pesticide and functional material, and can effectively reduce the preparation economy of medicine, pesticide and functional material into
This, and provide its friendly to environment.
Specific embodiment
In order to which technical problems, technical solutions and advantageous effects to be solved by the present invention are more clearly understood, below in conjunction with
Embodiment, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only used to explain
The present invention is not intended to limit the present invention.
In the embodiment of the present invention involved compound and its derivative be according to IUPAC (international purely and application
Credit union of student's federation) or the name of CAS (chemical abstracts service, positioned at Columbus, Ohio city) naming system.Therefore, it is of the invention
The compound group being specifically related in embodiment does following illustrate and explanation：
About " hydrocarbon group ", the minimum value of carbon content and maximum value are represented by prefix in hydrocarbon group, for example,
Prefix (Ca-Cb) any alkyl containing " a " to " b " a carbon atom of alkyl expression.Thus, for example, (C1-C6) alkyl refers to include
The alkyl of one to six carbon atom.
" alkoxy " refers to the straight chain of an oxygen atoms bond or with branch, monovalent, saturated aliphatic chain, including but
It is not limited to such as methoxyl group, ethyoxyl, propoxyl group, butoxy, isobutoxy, tert-butoxy and other similar groups.(Ca-Cb)
Alkoxy refer to any alkyl containing " a " to " b " a carbon atom and an oxygen atoms bond straight chain or with it is branch, monovalent,
Saturated aliphatic chain.
" alkyl " refers to straight chain or with branch, monovalent, saturated aliphatic chain, including but not limited to as methyl, ethyl,
Propyl, isopropyl, butyl, isobutyl group, amyl, isopentyl, hexyl and other similar groups.
" miscellaneous alkyl " refers to straight chain or with saturated aliphatic chain that is branch, monovalent, being connect at least one hetero atom,
Such as, but not limited to methylaminoethyl or other similar groups.
" alkenyl " refers to the linear chain or branch chain hydrocarbon with one or more double bonds, including but not limited to such as vinyl, propylene
Base and other similar groups.
" miscellaneous thiazolinyl " refers to the linear chain or branch chain hydrocarbon being connect at least one hetero atom with one or more double bonds, packet
It includes but is not limited to such as ethyleneamino ethyl or other similar groups.
" alkynyl " refers to the linear chain or branch chain hydrocarbon with one or more three keys, including but not limited to such as acetenyl, propine
Base and other similar groups.
" miscellaneous alkynyl " refers to the linear chain or branch chain hydrocarbon being connect at least one hetero atom with one or more three keys, packet
It includes but is not limited to such as acetenyl, propinyl and other similar groups.
" aryl " refers to a kind of cricoid aromatic hydrocarbon, including but not limited to such as phenyl, naphthalene, anthryl, phenanthryl and other
Similar group.
" heteroaryl " refers to monocyclic or polycyclic or polycyclic aromatic hydrocarbon, and one or more of carbon atoms are by such as nitrogen, oxygen
Or the hetero atoms such as sulphur substitution.If heteroaryl contains more than one hetero atom, these hetero atoms may be identical, it is also possible to
Different.Heteroaryl includes but not limited to such as benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzo thiophene
Oxazolyl, benzopyranyl, furyl, imidazole radicals, indazolyl, indolizine base, indyl, isobenzofuran-base, isoindolyl, isoquinoline
Quinoline base, isothiazolyl, isoxazolyl, naphthyridines Ji, oxadiazolyl, oxazinyl, oxazolyls, phthalazinyl, pteridyl, purine radicals, pyrrole
It mutters base, pyrazinyl, pyrazolyl, pyridazinyl, pyridine [3,4-b] indyl, pyridyl group, pyrimidine radicals, pyrrole radicals, quinolizine base, quinoline
Base, quinoxalinyl, thiadiazolyl group, thiatriazole base, thiazolyl, thienyl, triazine radical, triazolyl, xanthyl and other similar
Group.
" cycloalkyl " refers to the monocyclic or multi-ring alkyl of saturation, may be condensed with aromatic hydrocarbon group.Cycloalkyl includes but unlimited
In such as cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, suberyl, indanyl, tetrahydro naphthyl and other similar groups.
" Heterocyclylalkyl " refers to the monocyclic or multi-ring alkyl of saturation, may be condensed with an aromatic hydrocarbon group, wherein at least there is one
A carbon atom is taken by such as hetero atoms such as nitrogen, oxygen or sulphur and replaces.If Heterocyclylalkyl contains more than one hetero atom, these miscellaneous originals
Son may be identical, it is also possible to different.Heterocyclylalkyl includes but not limited to such as azabicyclic heptane base, azetidine
Base, indolinyl, morpholinyl, piperazinyl, piperidyl, pyrrolidinyl, tetrahydrofuran base, tetrahydric quinoline group, dihydro-indazol base,
Tetrahydro indole base, tetrahydro isoquinolyl, THP trtrahydropyranyl, tetrahydroquinoxaline base, tetrahydro thiapyran base, thiazolidinyl, thiomorpholine
Base, thioxanthene base, thiophene oxane base and other similar groups.
" cycloalkenyl group " refers to undersaturated, the monocyclic or polycycloalkenyl with one or more double bonds, may be with aromatic hydrocarbon group
It condenses, including but not limited to cyclic vinyl, cyclopropanyl or other similar groups.
" heterocycloalkenyl " refers to undersaturated, the monocyclic or polycycloalkenyl with one or more double bonds, may be with aryl
Group is condensed, and wherein at least one carbon atom is taken and replaced by such as nitrogen, oxygen or sulphur hetero atom.If Heterocyclylalkyl contains more than one
Hetero atom, then these hetero atoms may be identical, it is also possible to different.
" cycloalkynyl radical " refers to undersaturated, the monocyclic or polycyclic alkynyl with one or more three keys, may be with aromatic hydrocarbon group
It condenses, including but not limited to ring acetenyl, cyclopropyne base or other similar groups.
" heterocycle alkynyl " refers to undersaturated, the monocyclic or polycyclic alkynyl with one or more three keys, may be with aryl
Group is condensed, and wherein at least one carbon atom is taken and replaced by such as nitrogen, oxygen or sulphur hetero atom.If Heterocyclylalkyl contains more than one
Hetero atom, then these hetero atoms may be identical, it is also possible to different.
The embodiment of the present invention provides a kind of preparation method of compound aryl trifluoromethyl, including at least following steps：
Under illumination condition and alkaline condition, make compound A and trifluoromethyl reagent in the organic solvent containing catalyst
It reacts in system, obtains compound aryl trifluoromethyl；
The structural formula of wherein described compound A is as follows：
The R in the Compound A structure formula is alkyl, halogen, nitro, alkoxy, hydroxyl, one kind in carboxyl or
It is two or more.
Further details of explanation is done to the preparation method of compound aryl trifluoromethyl of the present invention below.
In the illumination condition of the present invention, preferred optical wavelength is 430nm-550nm, under the light-wave irradiation of the wavelength,
It may not need the catalysis of transition metal copper or palladium compound, it is not required that using particular functional group as activated group.
The present invention needs to form alkaline condition using base reagent.Preferably, the base reagent is organic base or inorganic base.
Organic base or inorganic base can form effective alkaline environment, and alkaline atmosphere is provided for synthesizing aryl trifluoromethyl compound.
It is further preferable that the organic base is amine organic base.
It is further preferred that the amine organic base is triethylamine, in diisopropyl ethyl amine, tetramethylethylenediamine
It is at least one.
Preferably, the inorganic base is lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, saleratus, phosphoric acid
Sodium, dibastic sodium phosphate, sodium dihydrogen phosphate, potassium phosphate, potassium hydrogen phosphate, potassium dihydrogen phosphate, potassium pyrophosphate sodium methoxide, sodium ethoxide, ethyl
At least one of sodium mercaptides.Inorganic base is weak base, is conducive to the progress of reaction under the conditions of weak base.
Preferably, the alkyl in the Compound A structure formula is C1-C20Alkyl.The halogen is fluorine, in chlorine, bromine, iodine
It is any.
Preferably, the trifluoromethyl reagent is any one of as described below for structural formula：
CF3SO2Cl、
Preferably, the catalyst is any one of acridinium salt or is any one of ruthenium catalyst.Using acridine
Salt or ruthenium catalyst are as catalyst, at the end of reaction, catalyst noresidue in target product is reacted.
Preferably, the acridinium salt is any one of as described below for structural formula：
Preferably, the ruthenium catalyst is any one of as described below for structural formula：
Preferably, the organic solvent is dimethylformamide (DMF), acetonitrile, methanol, ethyl alcohol, Isosorbide-5-Nitrae-dioxane, four
Any one of hydrogen furans, dimethyl sulfoxide (DMSO) (DMSO).For those of ordinary skills, according to herein described anti-
Other solvents that can be substituted can should be easily selected with disclosure.In one embodiment, what is added in is organic molten
The amount of agent, reaction raw materials can be completely dissolved.
Preferably, in the reaction system, the compound A, trifluoromethyl reagent, catalyst molar ratio be 1000：
(1000-4000)：(1-50).
In above-mentioned reaction raw materials under the effect of when illumination condition so that the reaction temperature model that above-mentioned reaction system is applicable in
Enclose is 0-80 DEG C.
In order to further improve reaction efficiency, in one embodiment, the reaction temperature of above-mentioned reaction system is 20~25 DEG C.
In another embodiment, the reaction temperature of above-mentioned reaction system is 22~25 DEG C.In each temperature preferably reacted
The time reacted in environment should cause above-mentioned reactant fully to react, if the reaction time can be 6-48 hours or longer anti-
Between seasonable.
The preparation method of compound aryl trifluoromethyl of the present invention, reaction condition is simple, and reaction raw materials only light requirement shines, alkalinity
The effect of condition and catalyst, you can obtain compound aryl trifluoromethyl, preparation process without ligand, without precursor chemical combination
Object, product are remained without catalyst.
On the other hand, based on compound aryl trifluoromethyl described above and preparation method thereof, since it has uniqueness
Chemical property and bioactivity, dipole moment, the polarity of compound can be significantly changed when being introduced into organic compound,
Lipophilicity and chemistry and metabolic stability, therefore, the compound aryl trifluoromethyl can be widely applied to medicine, pesticide,
In the preparation of functional material.Specifically such as, the Prozac for medicament for treatment of depression, the Yi Feiwei for treating AIDS-treating medicine
In human relations, the celecoxib for medicament for treating arthritis and the Sorafenib drug for antitumor drug.
In conjunction with embodiment, the present invention will be described in further detail.
Embodiment 1
The present embodiment provides a kind of preparation methods of 4- trifloro methyl phenols.The structural formula of the 4- trifloro methyl phenols is as follows
Shown in molecular structural formula I1：
Its preparation process is as follows：
Into drying, clean reaction vessel, 1mmol phenol, 2mmol CF are added in3SO2MeCN, 2mmol of Cl, 2mL
K2HPO4, while add in the acridinium salt of 0.05mmolUnder white light illumination, it stirs for 24 hours.
After reaction, reaction is also poured into water, and ethyl acetate extraction extracts three times, merges organic phase, anhydrous sulphur repeatedly
The drying of sour sodium, concentrates organic phase, obtains crude product, column chromatography for separation, obtains purified, and product is colourless liquid, yield 87%.
Relevant characterization is analyzed, as a result：13C NMR(CDCl3,200MHz,ppm)delta 157.8,127.3,
123.9 (q, 1J=360.0Hz), 123.0 (q, 1J=48.0Hz), 115.4；19FNMR(376MHz,CDCl 3)δ(ppm):-
62.7(3F,s)；MS(ESI-):161。
The result further demonstrates product molecule structure as above-mentioned molecular structure I1.
Embodiment 2
The present embodiment provides a kind of preparation methods of 1,4- dimethoxys -2- trifluoromethyls-benzene.The 1,4- dimethoxys-
Shown in the following molecular structural formula I2 of structural formula of 2- trifluoromethyls-benzene：
Its preparation process is as follows：
Into drying, clean reaction vessel, 1mmol Isosorbide-5-Nitraes-dimethoxy benzene, 4mmol CF are added in3SO2Cl, 2mL's
MeCN、2mmol K2HPO4, while add in the ruthenium catalyst of 0.05mmolIn white light
Under, stir 36h.
After reaction, reaction solution is poured into water, and ethyl acetate extraction, extraction three times, merges organic phase, anhydrous sodium sulfate
It is dry, organic phase is concentrated, obtains crude product, column chromatography for separation is carried out to the crude product, obtains purified, product is solid for white
Body, yield 79%.
The product I2 of preparation is subjected to characterize data analysis, as a result：1HNMR(400MHz,CDCl3)δ(ppm):
7.12 (s, 1H), 7.02 (d, 1H), 6.94 (d, 1H), 3.86 (s, 3H), 3.80 (s, 3H)19FNMR(376MHz,CDCl3)δ
(ppm):-62.9(3F,s)；MS(ESI+):207.The result further demonstrates product molecule structure as above-mentioned molecular structure
I2。
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
All any modification, equivalent and improvement made within refreshing and principle etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of compound aryl trifluoromethyl, includes the following steps：
Under illumination and alkaline condition, compound A and trifluoromethyl reagent is made to be sent out in the organic solvent system containing catalyst
Raw reaction, obtains compound aryl trifluoromethyl；
The structural formula of wherein described compound A is as follows：
A、
The R in the Compound A structure formula is one or both of alkyl, halogen, nitro, alkoxy, hydroxyl, carboxyl
More than.
2. preparation method according to claim 1, it is characterised in that：The compound A, trifluoromethyl reagent, catalyst
Molar ratio be 1000：(1000-4000)：(1-50).
3. preparation method according to claim 1, it is characterised in that：The optical wavelength of the illumination condition is 430-
550nm；And/or base reagent used in the alkaline condition is organic base or inorganic base.
4. according to any preparation method of claims 1 or 2, it is characterised in that：The catalyst is urged for acridinium salt or ruthenium
Any one of agent.
5. preparation method according to claim 4, it is characterised in that：The acridinium salt for structural formula such as
Described is any；
And/or the ruthenium catalyst for structural formula such asInstitute
Any one of state.
6. preparation method according to claim 3, it is characterised in that：The organic base at least one of amine or
The inorganic base is lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, saleratus, sodium phosphate, dibastic sodium phosphate, phosphorus
In acid dihydride sodium, potassium phosphate, potassium hydrogen phosphate, potassium dihydrogen phosphate, potassium pyrophosphate sodium methoxide, sodium ethoxide, ethanethio sodium at least
It is a kind of.
7. preparation method according to claim 1, it is characterised in that：The reaction temperature of the reaction is 0-80 DEG C.
8. preparation method according to claim 1, it is characterised in that：Any that the trifluoromethyl reagent is as follows
Kind：CF3SO2Cl、
9. according to compound aryl trifluoromethyl prepared by any preparation methods of claim 1-8 medicine, pesticide and
Application in the preparation of functional material.
10. application as claimed in claim 9, it is characterised in that：The application is used for for the compound aryl trifluoromethyl
Prepare any one of Prozac, efavirenz, celecoxib, Sorafenib.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107973800A (en) * | 2017-12-29 | 2018-05-01 | 深圳蓝新科技有限公司 | The preparation method of Zaleplon |
| CN109092362A (en) * | 2018-07-25 | 2018-12-28 | 大连理工大学 | The organic preparation method and application with polymers of triphenylamine base metal with visible light catalytic heteroaromatic compounds trifluoromethylation performance |
| CN111423331A (en) * | 2019-01-10 | 2020-07-17 | 北京工商大学 | Photochemical catalytic synthesis method of aryl alkyl ether |
| CN115417751A (en) * | 2022-06-13 | 2022-12-02 | 中山大学 | Method for hydroxylation of benzene ring C-H phenol |
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2017
- 2017-12-29 CN CN201711489777.9A patent/CN108191612A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107973800A (en) * | 2017-12-29 | 2018-05-01 | 深圳蓝新科技有限公司 | The preparation method of Zaleplon |
| CN109092362A (en) * | 2018-07-25 | 2018-12-28 | 大连理工大学 | The organic preparation method and application with polymers of triphenylamine base metal with visible light catalytic heteroaromatic compounds trifluoromethylation performance |
| CN109092362B (en) * | 2018-07-25 | 2021-07-06 | 大连理工大学 | Preparation method and application of triphenylamine-based metal organic coordination polymer with visible light catalytic aromatic heterocyclic compound trifluoromethyl performance |
| CN111423331A (en) * | 2019-01-10 | 2020-07-17 | 北京工商大学 | Photochemical catalytic synthesis method of aryl alkyl ether |
| CN111423331B (en) * | 2019-01-10 | 2022-11-11 | 北京工商大学 | Photochemical catalytic synthesis method of aryl alkyl ether |
| CN115417751A (en) * | 2022-06-13 | 2022-12-02 | 中山大学 | Method for hydroxylation of benzene ring C-H phenol |
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Application publication date: 20180622 |