CN115785007A - Method for synthesizing ketone compound by illumination - Google Patents
Method for synthesizing ketone compound by illumination Download PDFInfo
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- CN115785007A CN115785007A CN202211588916.4A CN202211588916A CN115785007A CN 115785007 A CN115785007 A CN 115785007A CN 202211588916 A CN202211588916 A CN 202211588916A CN 115785007 A CN115785007 A CN 115785007A
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- -1 ketone compound Chemical class 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000005286 illumination Methods 0.000 title claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 150000004715 keto acids Chemical class 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 230000010933 acylation Effects 0.000 claims abstract description 6
- 238000005917 acylation reaction Methods 0.000 claims abstract description 6
- 239000007800 oxidant agent Substances 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 3
- 230000000996 additive effect Effects 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 3
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 229910052710 silicon Inorganic materials 0.000 claims 3
- 239000010703 silicon Substances 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 238000006552 photochemical reaction Methods 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 38
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000013341 scale-up Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 description 14
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- IIYVNMXPYWIJBL-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1 IIYVNMXPYWIJBL-UHFFFAOYSA-N 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 244000221633 Brassica rapa subsp chinensis Species 0.000 description 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 1
- 238000006641 Fischer synthesis reaction Methods 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LFABNOYDEODDFX-UHFFFAOYSA-N bis(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=C(Br)C=C1 LFABNOYDEODDFX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Abstract
The invention discloses a novel method for synthesizing various ketone compounds by decarboxylation and acylation of nitrogen heterocycles through keto acid under the condition of no solvent in illumination, and relates to the technical field of synthesis of medicines and materials. The synthesis method comprises the following steps: under the irradiation of light, keto acid and nitrogen heterocyclic compound are mixed and reacted in an open atmosphere at room temperature to obtain heterocyclic acylation product. The synthesis method has the following characteristics: 1) No solvent is needed; 2) No photosensitizer, oxidant or additive is needed; 3) The scale-up can be carried out to kilogram-level production; 4) The reaction rate is faster with larger amount of substrate. Therefore, the method can be widely applied to large-scale synthesis production of corresponding medicines, intermediates and materials.
Description
Technical Field
The invention relates to the technical field of medicine and material synthesis, in particular to a novel method for green synthesis of heterocyclic ketone compounds under the condition of illumination and no solvent.
Background
A large number of natural products and drug molecules belong to the nitrogen heterocyclic carbonyl compounds and derivatives thereof. Also, the ketocarbonyl group can undergo rich functional group transformations. Such as: synthesizing corresponding olefin through a Wittig reaction; synthesizing alcohol by a Barbier-Grignard reaction; synthesizing corresponding alkane through Clemmensen reduction or Wolff-Kishner-Huang Minlon reaction; indole is synthesized by Fischer reaction. Therefore, the green and efficient synthesis of ketone compounds occupies an extremely high position in the synthesis of medicaments.
According to the reports of the literature, the existing synthesis methods of the nitrogen heterocyclic ring substituted ketone compounds include the following methods:
(1) By oxidation of the corresponding alcohol
The disadvantages are that: the method needs to synthesize the corresponding alcohol firstly, and often needs to use a large amount of chemical oxidants to complete the oxidation, and the chemical oxidants mostly cause serious environmental pollution.
(2) Acylation of pakchoi
The disadvantages are as follows: the use of moisture and water sensitive acid halides; also large amounts of lewis acids are required; and the friedel-crafts acylation is generally only applicable to electron rich aromatic or heterocyclic aromatic hydrocarbons.
(3) Free radical acylation
The disadvantages are as follows: the reported radical acylation strategies generally require transition metal or photosensitizer catalysis, and most of them require the use of a large amount of chemical oxidizing agents.
In conclusion, the existing methods for synthesizing the azacyclic ketone compounds have obvious defects and need to be improved. It is particularly noteworthy that all the methods reported in the past require the use of large amounts of solvent.
Disclosure of Invention
The invention aims to create a novel, green and safe novel method capable of industrially synthesizing the nitrogen heterocyclic ring substituted ketone compound.
The invention provides a method for synthesizing heterocyclic ketone compounds under the condition of no solvent. The method comprises the following steps: under the condition of illumination and no solvent, nitrogen heterocyclic compounds and ketonic acid are mixed and subjected to open reaction at room temperature, and the ketone compounds substituted by nitrogen heterocyclic rings can be obtained. The specific synthetic method is shown as the following formula:
the invention has the beneficial effects that: the invention relates to a first example of a method for industrially synthesizing azocyclic ketone compounds under the solvent-free condition. Compared with the existing synthesis process, the method is green, safe, economical, simple and convenient, and does not need any catalyst, oxidant, additive and solvent; the reaction condition is mild, the reaction can be completed in a room-temperature open system without the conditions of high temperature, high pressure, no water, no oxygen and the like; even without stirring; the cost is low; the equipment is simple; the operation is simple and convenient; the scale-up can be carried out to kilogram-level production; therefore, the method disclosed by the invention can be widely applied to the industrial production of medicines and new materials.
The invention provides a novel method for synthesizing azacyclic ketone compounds with greenness, high efficiency, safety and low consumption, which comprises the following steps:
in a reactor, mixing nitrogen heterocyclic compound and keto acid, starting a light source, carrying out an open reaction at room temperature, monitoring the reaction process, turning off the light source after the reaction is finished, and carrying out recrystallization or reduced pressure distillation or column chromatography separation to obtain the product.
Detailed Description
The process of the present invention will be further illustrated by the following examples, but the present invention is not limited to these examples.
Example 1:
quinoxaline (130.0 g,1.0mol,1.0 eq.), phenylketoacid (150.0 g,1.0mol,1.0 eq.) was placed in a reaction vessel; the blue light lamp was turned on for 1 hour. After the reaction was completed, the product was obtained by recrystallization or column chromatography with a yield of 88%.
Example 2:
quinoxaline (130.0g, 1.0mol,1.0 eq.), phenylketo acid (150.0g, 1.0mol, 1.0eq.) is placed in a reaction vessel; the ultraviolet lamp was turned on for 1 hour. After completion of the reaction, recrystallization or column chromatography gave the product in 82% yield.
Example 3:
quinoxaline (130.0g, 1.0mol, 1.0eq.) and phenylketo acid (150.0g, 1.0mol, 1.0eq.) are placed in a reaction vessel; the incandescent lamp was turned on for 1 hour. After the reaction was completed, recrystallization or column chromatography gave a product in a yield of 70%.
Example 4:
quinoxaline (1300.0 g,10.0mol,1.0 eq.), phenylketonic acid (1500.0 g,10.0mol,1.0 eq.) was placed in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, recrystallization or column chromatography gave a product with a yield of 95%.
Example 5:
quinoxaline (1300.0 g,10.0mol,1.0 eq.), pyruvic acid (880.0 g,10.0mol,1.0 eq.) was placed in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, recrystallization or column chromatography gave a product in 96% yield.
Example 6:
4, 7-dichloroquinoline (1970.0 g,10.0mol,1.0 eq.), phenylketonic acid (1500.0 g,10.0mol,1.0 eq.) were placed in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, recrystallization or column chromatography gave the product in 90% yield.
Example 7:
placing isoquinoline (1290.0g, 10.0mol, 1.0eq.) and phenylketonic acid (1500.0g, 10.0mol, 1.0eq.) in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, recrystallization or column chromatography gave the product in 92% yield.
Example 8:
placing N-methylpyrrole (810.0g, 10.0mol, 1.0eq.) and p-methyl benzonic acid (1640.0g, 10.0mol, 1.0eq.) in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After completion of the reaction, recrystallization or column chromatography gave the product in 91% yield.
Example 9:
4-trifluoromethylpyridine (1470.0 g,10.0mol,1.0 eq.), phenylketonic acid (1500.0 g,10.0mol,1.0 eq.) was placed in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After completion of the reaction, recrystallization or column chromatography gave the product in 93% yield.
Example 10:
placing the quinoxalinone derivative (2360.0 g,10.0mol,1.0 eq.) 4-bromophenylketone acid (2280.0 g,10.0mol,1.0 eq.) in the above formula in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, recrystallization or column chromatography gave the product in 86% yield.
Example 11:
placing the isoquinoline derivative (2950.0 g,10.0mol,1.0 eq.) and phenylketonic acid (1500.0 g,10.0mol,1.0 eq.) in the above formula in a reaction vessel; and turning on a blue light lamp for illumination for 1 minute. After the reaction was completed, the product was obtained by recrystallization or column chromatography with a yield of 89%.
Example 12:
quinoxaline (130.0 g,1.0mol,1.0 eq.), phenylketoacid (150.0 g,1.0mol,1.0 eq.) was placed in a reaction vessel; reducing the temperature of the reaction system from room temperature to 0 ℃; the blue light lamp was turned on for 1 hour. After the reaction was completed, recrystallization or column chromatography gave the product in 85% yield.
Example 13:
quinoxaline (130.0 g,1.0mol,1.0 eq.), phenylketoacid (150.0 g,1.0mol,1.0 eq.) was placed in a reaction vessel; raising the temperature of the reaction system from room temperature to 80 ℃; the ultraviolet lamp was turned on for 1 hour. After the reaction was completed, recrystallization or column chromatography gave the product in 90% yield.
Attached table I, comparison of light reaction conditions in different media
Reaction conditions are as follows: azacyclo (5mmol, 1eq.); keto acid (5mmol, 1eq.); and (5) irradiating by a 24W blue light lamp at the room temperature of 20-25 ℃.
In the second attached Table, the azacyclic and keto acids considered in the invention and their products, yields are selected (without being limited to these substrates)
Reaction conditions are as follows: azacyclo (10mmol, 1eq.); keto acids (10mmol, 1eq.); and (5) irradiating by a 24W blue light lamp at the room temperature of 20-25 ℃.
Claims (6)
1. A method for synthesizing ketone compounds by illumination is characterized in that keto acid and nitrogen heterocyclic compounds are directly mixed and contacted under the illumination condition, and are irradiated by a light source under the room temperature condition to obtain heterocyclic acylation products.
2. The method for synthesizing ketone compounds by illumination according to claim 1, wherein the light source is a light source having a wavelength of 10nm to 780 nm.
3. The method for synthesizing ketone compound by illumination according to claim 1, wherein the photochemical reaction does not require a solvent, a photosensitizer, an oxidant, or an additive.
4. The method for synthesizing ketone compound by illumination according to claim 1, wherein the temperature of the photochemical reaction is in a range of 0 to 80 ℃.
5. The method for synthesizing ketone compounds by illumination according to claim 1, wherein the keto acid is the following compound:
wherein R and R' are respectively hydrogen or aryl or heterocyclic aryl or alkyl or cycloalkyl or alkyl or aryl with halogen, oxygen, nitrogen, silicon, phosphorus and sulfur atoms; or R and R' are linked together to form an alicyclic or aromatic ring compound,
the heterocyclic compound is the following compound:
wherein R, R 'and R' are independently hydrogen or halogen atoms or aryl or heterocyclic aryl or alkyl or cycloalkyl or alkyl or aryl groups with halogen, oxygen, nitrogen, silicon, phosphorus or sulfur atoms attached; or R and R' are linked together to form an alicyclic or aromatic ring compound,
the product is the following compound:
wherein R, R 'and R' are respectively hydrogen or halogen atom or aryl or heterocyclic aryl or alkyl or cycloalkyl or alkyl or aryl with halogen, oxygen, nitrogen, silicon, phosphorus or sulfur atom; or R and R' are linked together to form an alicyclic or aromatic ring compound.
6. The method for synthesizing ketone compounds by illumination according to claim 5, wherein the halogen atom is: fluorine, chlorine, bromine or iodine.
Priority Applications (1)
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| CN202211588916.4A CN115785007A (en) | 2022-12-10 | 2022-12-10 | Method for synthesizing ketone compound by illumination |
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| CN202211588916.4A CN115785007A (en) | 2022-12-10 | 2022-12-10 | Method for synthesizing ketone compound by illumination |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892545A (en) * | 2020-08-31 | 2020-11-06 | 怀化学院 | Green synthesis method of 1-methyl-3-alkyl quinoxalinone compound |
| CN111978201A (en) * | 2020-10-09 | 2020-11-24 | 甘肃农业大学 | Synthesis method of N, N' -diaryl benzoyl hydrazine compound |
| CN113620891A (en) * | 2021-09-09 | 2021-11-09 | 浙江树人学院（浙江树人大学） | Method for preparing quinoxaline-2-ketone derivative by controllable catalysis |
| CN114436793A (en) * | 2022-01-25 | 2022-05-06 | 赣南医学院 | Method for synthesizing mild alpha, alpha' -diaryl ketone |
-
2022
- 2022-12-10 CN CN202211588916.4A patent/CN115785007A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892545A (en) * | 2020-08-31 | 2020-11-06 | 怀化学院 | Green synthesis method of 1-methyl-3-alkyl quinoxalinone compound |
| CN111978201A (en) * | 2020-10-09 | 2020-11-24 | 甘肃农业大学 | Synthesis method of N, N' -diaryl benzoyl hydrazine compound |
| CN113620891A (en) * | 2021-09-09 | 2021-11-09 | 浙江树人学院（浙江树人大学） | Method for preparing quinoxaline-2-ketone derivative by controllable catalysis |
| CN114436793A (en) * | 2022-01-25 | 2022-05-06 | 赣南医学院 | Method for synthesizing mild alpha, alpha' -diaryl ketone |
Non-Patent Citations (3)
| Title |
|---|
| LONG-YONG XIE ET AL.: "Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions", 《GREEN CHEMISTRY》, vol. 22, 6 February 2020 (2020-02-06), pages 1720 - 1725 * |
| 关保川等: "可见光催化脱羧偶联反应研究进展", 《有机化学》, vol. 36, 31 December 2016 (2016-12-31), pages 1564 - 1571 * |
| 阮利衡等: "光诱导酰基自由基反应的研究进展", 《有机化学》, vol. 38, 31 December 2018 (2018-12-31), pages 3155 - 3164 * |
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