CN114832862A - Catalytic composition for coupling reaction and application thereof in preparation of isoquinoline-1, 3-diketone compounds - Google Patents
Catalytic composition for coupling reaction and application thereof in preparation of isoquinoline-1, 3-diketone compounds Download PDFInfo
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- 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
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- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
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Abstract
The invention provides a catalytic composition for coupling reaction and application thereof in preparation of isoquinoline-1, 3-diketone compounds, wherein the catalytic composition comprises a nickel catalyst, a ligand and a cocatalyst, the cocatalyst is halide, and the molar ratio of the nickel catalyst to the ligand to the cocatalyst is 1: 1-3: 30-40, the nickel catalyst exists in one or more of organic matters and inorganic matters, the valence of the nickel is 0 and +2, and the inorganic matters are divalent and non-oxide. The catalyst composition has the advantages of low price, easy obtainment, convenient operation, mild reaction condition, wide substrate range and the like.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a catalytic composition for coupling reaction and application thereof in preparation of isoquinoline-1, 3-diketone compounds.
Background
Isoquinoline-1, 3-diketone compounds as an important nitrogen-containing heterocyclic compound widely exist in natural products and medicines with biological activity, so that new functional groups are introduced into the skeleton, and more opportunities are provided for discovering new bioactive molecules. It is known that the chemical and physical properties of bioactive compounds can be modified by the addition of fluorine-containing groups, and the fluorine-containing groups have higher solubility and lipophilicity, so that the permeability and bioavailability of cell membranes are improved. Therefore, how to introduce fluorine-containing groups into the structure of isoquinoline-1, 3-dione compounds becomes a hot spot for organic chemists to study.
In 2017, Wang developed a method for preparing CF-containing compound by performing direct difluoromethylation reaction on methacrylamide through visible light catalysis 2 H/CF 3 The method of isoquinoline-1, 3-diones (G.L.Zou, X.L.Wang, org.Biomol.chem.,2017,15, 8748-one 8754.). In 2016, Wang et al successfully developed an efficient Pd-catalyzed difluoroalkylation/cyclization reaction to synthesize isoquinoline-1, 3-diones (X.F.Xia, S.L.Zhu, Y.Li, H.J.Wang, RSC adv.,2016,6, 51703-. Although a lot of reports exist for introducing fluorine-containing groups into an isoquinoline-1, 3-diketone structure, the reaction conditions are strict, the substrate range is narrow, an expensive metal catalyst is also used, the reaction cost is high, and the economic and environment-friendly principle is not met.
Disclosure of Invention
To overcome these limitations, the direct introduction of fluorinated groups into aromatic rings by transition metal catalyzed cross-coupling reactions is a direct route to valuable difluoroalkylated frameworks. The nickel catalyst is cheap, easy to obtain, economical and applicable, and more importantly, the nickel catalyst is low in electronegativity and high in oxidative addition activity, and can effectively avoid partial side reactions. The invention aims to provide a coupling reaction catalytic composition with low cost and mild reaction conditions and application thereof in preparation of isoquinoline-1, 3-diketone compounds.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a catalytic composition for coupling reaction, which comprises a nickel catalyst, a ligand and a cocatalyst, wherein the cocatalyst is halide, and the molar ratio of the nickel catalyst, the ligand and the cocatalyst is 1: 1-3: 30-40, the nickel catalyst exists in one or more of organic matters and inorganic matters, the valence of the nickel is 0 and +2, and the inorganic matters are divalent and non-oxide. The cocatalyst is used for improving the activity of the nickel catalyst, and commonly used halides such as magnesium chloride, sodium iodide, potassium iodide, trimethylchlorosilane and the like are used. The nickel catalyst can be organic nickel catalyst, inorganic nickel catalyst, preferably halogenated nickel.
As a further improvement of the technical scheme, in order to improve the catalytic effect, the nickel catalyst is nickel bromide.
As a further improvement of the technical scheme, the cocatalyst is anhydrous magnesium chloride.
As a further improvement of the technical scheme, the ligands are nitrogen-containing ligands and phosphine ligands.
As a further improvement of the technical scheme, in order to improve the yield, the ligand is 2,2 '-dipyridyl-4, 4' -dicarboxylic acid methyl ester (L1) and 1, 2-bis (diphenylphosphino) ethane (DPPE).
The application of the catalytic composition in preparing isoquinoline-1, 3-diketone compounds comprises the following steps: under the action of the catalytic composition and a reducing agent, the o-iodoacryloyl benzamide compound I and the difluoro compound II are subjected to coupling reaction in a solvent to obtain an isoquinoline-1, 3-diketone compound, wherein the reaction route is as shown in formula (I):
in the formula (I), R 1 Is 1 or more substituents of the phenyl ring to which it is attached, each R 1 Independently selected from hydrogen, halogen or methyl; r 2 Is C1-C4 alkyl, phenyl or benzyl; r is 3 Is C1-C4 alkyl; r 4 Is morpholine, -N (Et) 2 or-OCH 2 CH 3 . The reaction temperature of the application is 25-80 ℃, and the reaction condition is mild.
During catalysis, a nickel catalyst and a ligand form a compound, an intermediate is formed through oxidation addition and migration insertion, Ni on the intermediate undergoes valence state change under the action of a reducing agent, and after the reaction is finished, the removed Ni ligand compound returns to the initial state under the action of the reducing agent.
After the o-iodoacryloyl benzamide compound and the difluoro compound are subjected to metal catalytic coupling reaction, product separation and characterization can be carried out according to a conventional separation and purification method. Preferably, the post-treatment steps of the reaction liquid obtained after the metal-catalyzed coupling reaction of the o-iodoacryloyl benzamide compound and the difluoro compound are as follows: after the reaction is finished, cooling the reaction liquid to room temperature, quenching the reaction liquid by using a saturated ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, decompressing and concentrating to remove the solvent, separating and purifying the obtained crude product by using column chromatography to obtain an isoquinoline-1, 3-diketone product, wherein an eluent is a mixed solvent of ethyl acetate and petroleum ether, and the volume ratio of the ethyl acetate to the petroleum ether in the mixed solvent of the ethyl acetate and the petroleum ether is 0.05-0.1: 1.
As a further improvement of the technical scheme, in order to reduce the side reaction, the application is carried out under the condition of isolating air, and an inert atmosphere, such as nitrogen and an atmosphere of a group zero element, is adopted.
As a further improvement of the technical scheme, in order to reduce the reaction cost, R 1 Is hydrogen, halogen or methyl; r 2 Is C1-C4 alkyl, phenyl or benzyl; r 3 Is C1-C4 alkyl.
As a further improvement of the technical scheme, in order to improve the yield, the molar ratio of the nickel catalyst, the reducing agent and the o-iodoacryloyl benzamide compound is 0.05-0.15: 2-5: 1.
As a further improvement of the technical scheme, in order to improve the conversion rate, the molar ratio of the o-iodoacryloyl benzamide compound to the difluoro compound is 1: 1.5-3, preferably 1: 3.
As a further improvement of the technical scheme, the solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran, acetonitrile, 1, 4-dioxane and N-methylpyrrolidone.
Compared with the prior art, the catalyst composition has outstanding substantive characteristics and remarkable progress, and particularly, the catalyst composition adopts cheap and easily-obtained transition metal nickel as a main catalyst, and the cocatalyst and the ligand are conventional products and are low in price and easy to obtain. Furthermore, the catalyst composition provided by the invention is high in selectivity when used for preparing isoquinoline-1, 3-diketone compounds, and can effectively avoid side reactions. Furthermore, when the catalyst composition is used for preparing isoquinoline-1, 3-diketone compounds, the reaction conditions are mild, and the substrate range is wide. The catalyst composition has the advantages of low cost, easy obtaining, mild reaction conditions and wide substrate range.
Detailed Description
The technical solution of the present invention is further described in detail by the following embodiments.
Experimental procedures, in which specific conditions are not noted in the examples of the present disclosure, are generally performed under conventional conditions, or under conditions recommended by manufacturers of raw materials or commercial products. Reagents of specific sources are not indicated, and conventional reagents are purchased in the market.
Example 1
A process for preparing isoquinoline-1, 3-diones (IIIa) by nickel-catalyzed metal coupling, the reaction scheme being as follows:
the preparation method specifically comprises the following steps of adding a nickel catalyst (NiBr) into a 10ml Schlenk bottle 2 0.05mmol), ligand (L3, 0.05 mmol; DPPE, 0.05mmol), reducing agent (Mn, 1.5mmol), cocatalyst (MgCl) 2 2mmol), an o-iodoacryloyl benzamide compound (namely the raw material Ia, 0.5mmol), a difluoro compound (namely the raw material IIa, 1.5mmol) and 2ml of dimethyl sulfoxide are stirred and reacted under the condition of argon atmosphere and 60 ℃, and the reaction progress is detected by TLC until the raw material disappears (the reaction time is 24 hours). After the reaction is finished, cooling the reaction solution to room temperature, quenching the reaction solution by using a saturated ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, concentrating the mixture under reduced pressure to remove the solvent, and separating and purifying the obtained crude product by using column chromatography (eluent is ethyl acetate: petroleum ether-1: 20-1: 10, v/v) to obtain 95mg of a target product, wherein the yield is 52%.
The characterization data for isoquinoline-1, 3-diones (IIIa) are as follows:
1 H NMR(300MHz,Chloroform-d):δ8.29(d,J＝6.7Hz,1H),7.66–7.61(t,J＝7.5Hz，1H),7.50–7.41(m,2H),4.04–3.88(m,4H),3.39-3.24(m,1H),2.99–2.83(m,1H),1.66–1.58(m,5H),1.47–1.37(m,2H),1.21(t,J＝7.2Hz,3H),0.97(t,J＝7.3Hz,3H).
13 C{ 1 H}NMR(150MHz,Chloroform-d):δ174.57,163.52,163.21(d,J＝32.0Hz),140.65,133.34,129.16,127.86,125.97,124.70,114.46(dd,J＝255.4,250.8Hz),63.02,44.62(dd,J＝23.6,21.7Hz),43.56(d,J＝5.0Hz),40.58,31.76,29.57,20.26,13.80,13.66.
19 F{ 1 H}NMR(282MHz,Chloroform-d):δ-101.06(d,J＝255.6Hz),-104.83(d,J＝255.6Hz).
HRMS(ESI)m/z:[M+H] + Calcd for C 19 H 24 F 2 NO 4 368.1673；found 368.1687(+0.0014).
example 2
A process for preparing isoquinoline-1, 3-diones (IIIb) by nickel-catalyzed metal coupling, the reaction scheme being as follows:
the preparation method specifically comprises the following steps of adding a nickel catalyst (NiBr) into a 10ml Schlenk bottle 2 0.05mmol), ligand (L3, 0.05 mmol; DPPE, 0.05mmol), reducing agent (Mn, 1.5mmol), cocatalyst (MgCl) 2 2mmol), an o-iodoacryloyl benzamide compound (namely the raw material Ib, 0.5mmol), a difluoro compound (namely the raw material IIa, 1.5mmol) and 2ml of dimethyl sulfoxide are stirred and reacted under the condition of argon atmosphere and 60 ℃, and the reaction progress is detected by TLC until the raw material disappears (the reaction time is 24 hours). After the reaction is finished, cooling the reaction solution to room temperature, quenching the reaction solution by using a saturated ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, concentrating the mixture under reduced pressure to remove the solvent, and separating and purifying the obtained crude product by using column chromatography (eluent is ethyl acetate: petroleum ether-1: 20-1: 10, v/v) to obtain 102.8mg of a target product, wherein the yield is high51％。
The characterization data for isoquinoline-1, 3-diones (IIIb) are as follows:
1 H NMR(300MHz,Chloroform-d):δ8.23(d,J＝8.5Hz,1H),7.45(dd,J＝8.5,1.9Hz,1H),7.39(d,J＝1.8Hz,1H),4.12–3.98(m,4H),3.41–3.26(m,1H),2.94–2.78(m,1H),1.66–1.57(m,5H),1.44–1.36(m,2H),1.27(t,J＝7.2Hz,3H),0.97(t,J＝7.3Hz,3H).
13 C{ 1 H}NMR(125MHz,Chloroform-d):δ173.98,163.09(t,J＝32.3Hz),162.68,142.45,140.02,130.84,128.49,126.10,123.22,114.28(t,J＝253.6Hz)63.20,44.53(t,J＝22.7Hz),43.62(d,J＝4.7Hz),40.69,31.61,29.52,20.22,13.75,13.74.
19 F{ 1 H}NMR(282MHz,Chloroform-d):δ-99.84(d,J＝267.4Hz),-103.95(d,J＝267.4Hz).
HRMS(ESI)m/z:[M+H] + Calcd for C 19 H 23 ClF 2 NO 4 402.1284；found 402.1292(+0.0008).
example 3
A process for the preparation of isoquinoline-1, 3-diones (IIIc) by nickel-catalyzed metal coupling, the reaction scheme being as follows:
the preparation method specifically comprises the following steps of adding a nickel catalyst (NiBr) into a 10ml Schlenk bottle 2 0.05mmol), ligand (L3, 0.05 mmol; DPPE, 0.05mmol), reducing agent (Mn, 1.5mmol), cocatalyst (MgCl) 2 2mmol), an o-iodoacryloyl benzamide compound (namely the raw material IC, 0.5mmol), a difluoro compound (namely the raw material IIa, 1.5mmol) and 2ml of dimethyl sulfoxide are stirred and reacted under the condition of argon atmosphere and 60 ℃, and the reaction progress is detected by TLC until the raw material disappears (the reaction time is 24 hours). After the reaction is finished and the reaction liquid is cooled to room temperature, quenching the reaction liquid by using saturated ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, and removing the solvent by vacuum concentration to obtain the productThe crude product was purified by column chromatography (eluent ethyl acetate: petroleum ether: 1:20 to 1:10, v/v) to give 95mg of the desired product in 47% yield.
The characterization data for isoquinoline-1, 3-diones (IIIc) are as follows:
1 H NMR(300MHz,Chloroform-d):δ8.30(d,J＝7.9Hz,1H),7.64(t,J＝7.6Hz,1H),7.51–7.42(m,4H),7.35–7.29(m,2H),7.28–7.24(m,1H),5.29–5.17(m,2H),4.04–3.88(m,2H),3.42–3.27(m,1H),2.93(dt,J＝18.5,14.9Hz,1H),1.65(s,3H),1.21(t,J＝7.2Hz,3H).
13 C{ 1 H}NMR(125MHz,Chloroform-d):δ174.70,163.53,163.31(t,J＝31.8Hz),140.71,136.91,133.52,129.36,128.59,128.36,127.91,127.36,125.97,124.59,114.38(dd,J＝255.0,251.2Hz),63.01,44.34(t,J＝22.7Hz),43.94,43.89,31.89,13.66.
19 F{ 1 H}NMR(282MHz,Chloroform-d):δ-99.54(d,J＝266.3Hz),-103.88(d,J＝266.4Hz).
HRMS(ESI)m/z:[M+H] + Calcd for C 22 H 22 F 2 NO 4 402.1517；found 402.1519(+0.0002).
example 4
A method for preparing isoquinoline-1, 3-diketone compounds (IIId) by a nickel-catalyzed metal coupling reaction, which comprises the following steps:
the preparation method specifically comprises the following steps of adding a nickel catalyst (NiBr) into a 10ml Schlenk bottle 2 0.05mmol), ligand (L3, 0.05 mmol; DPPE, 0.05mmol), reducing agent (Mn, 1.5mmol), cocatalyst (MgCl) 2 2mmol), an o-iodoacryloyl benzamide compound (namely the raw material Id, 0.5mmol), a difluoro compound (namely the raw material IIa, 1.5mmol) and 2ml of dimethyl sulfoxide are stirred and reacted under the condition of argon atmosphere and 60 ℃, and the reaction progress is detected by TLC until the raw material disappears (the reaction time is 24 hours). After the reaction is finished, cooling the reaction liquid to room temperatureQuenching the mixture with an ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases with anhydrous sodium sulfate, concentrating the mixture under reduced pressure to remove the solvent, and separating and purifying the obtained crude product by column chromatography (eluent is ethyl acetate: petroleum ether-1: 20-1: 10, v/v) to obtain 62mg of a target product, wherein the yield is 33%.
The characterization data for isoquinoline-1, 3-diones (IIId) are as follows:
1 H NMR(300MHz,Chloroform-d):δ8.30(d,J＝7.9Hz,1H),7.65(t,J＝7.0Hz,1H),7.48(t,J＝7.6Hz,1H),7.37(d,J＝7.9Hz,1H),4.06–3.86(m,4H),3.35–3.21(m,1H),2.98–2.82(m,1H),2.37–2.30(m,1H),1.94–1.87(m,1H),1.64–1.59(m,2H),1.46–1.39(m,2H),1.21(t,J＝7.2Hz,3H),0.98(t,J＝7.3Hz,3H),0.50(t,J＝7.4Hz,3H).
13 C{ 1 H}NMR(125MHz,Chloroform-d):δ174.06,163.65,163.42(t,J＝38.7Hz),138.95,133.40,128.96,127.82,126.49,125.68,114.53(dd,J＝250.5,252.8Hz),62.98,48.28(d,J＝4.9Hz),44.92(dd,J＝24.0,21.5Hz),40.58,38.07,29.62,20.33,13.77,13.65,7.99.
19 F{ 1 H}NMR(282MHz,Chloroform-d):δ-98.60(d,J＝266.1Hz),-104.09(d,J＝266.1Hz).
HRMS(ESI)m/z:[M+H] + Calcd for C 20 H 26 F 2 NO 4 382.1830；found 382.1837(+0.0007).
example 5
A method for preparing isoquinoline-1, 3-diketone compounds (IIIe) by a nickel-catalyzed metal coupling reaction, which comprises the following steps:
the preparation method specifically comprises the following steps of adding a nickel catalyst (NiBr) into a 10ml Schlenk bottle 2 0.05mmol), ligand (L3, 0.05 mmol; DPPE, 0.05mmol), reducing agent (Mn, 1.5mmol), cocatalyst (MgCl) 2 2mmol), o-iodoacryloyl benzamide compound (namely, raw material Ia, 0.5mmol) and difluoro compoundThe reaction mixture (i.e., 1.5mmol of the starting IIe) and 2ml of dimethyl sulfoxide were stirred under argon atmosphere at 60 ℃ and the progress of the reaction was checked by TLC until the starting material disappeared (reaction time: 24 hours). After the reaction is finished, cooling the reaction solution to room temperature, quenching the reaction solution by using a saturated ammonium chloride solution, adding water and ethyl acetate for extraction for three times, combining organic phases, drying the organic phases by using anhydrous sodium sulfate, concentrating the mixture under reduced pressure to remove the solvent, and separating and purifying the obtained crude product by using column chromatography (eluent is ethyl acetate: petroleum ether-1: 20-1: 10, v/v) to obtain 120.2mg of a target product, wherein the yield is 59%.
The characterization data for isoquinoline-1, 3-diones (IIIe) are as follows:
1 H NMR(300MHz,Chloroform-d):δ8.27(dd,J＝8.3,1.3Hz,1H),7.63(t,J＝7.6Hz,1H),7.46(t,J＝7.8Hz,2H),4.01(dd,J＝8.3,6.8Hz,2H),3.68–3.47(m,9H),3.06–2.88(m,1H),1.67–1.55(m,5H),1.43–1.35(m,2H),0.95(t,J＝7.3Hz,3H).
13 C{ 1 H}NMR(125MHz,Chloroform-d):δ175.04,163.81,161.25(t,J＝28.5Hz),141.87,133.34,128.97,127.52,126.07,124.23,118.10(t,J＝257.1Hz),66.54,46.31(t,J＝6.2Hz),44.29(t,J＝20.5Hz),43.45,43.42,40.47,31.95,29.64,20.22,13.78.
19 F{ 1 H}NMR(282MHz,Chloroform-d):δ-95.43(d,J＝280.7Hz),-98.14(d,J＝280.6Hz).
HRMS(ESI)m/z:[M+H] + Calcd for C 21 H 27 F 2 N 2 O 4 409.1939；found 409.1944(+0.0005).
comparative example 1
This example differs from example 1 in that: no DPPE was added. The yield of the target product is 30%, and the yield is far lower than that of example 1, which shows that the reaction process can be accelerated and the reaction yield can be improved by adding the phosphine ligand.
Comparative example 2
This example differs from example 1 in that: adding a base. The yield of the target product was 0.
Comparative example 3
This example differs from example 1 in that: manganese powder is not added. The yield of the target product was 0.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention and not to limit it; although the present invention has been described in detail with reference to preferred embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention; without departing from the spirit of the present invention, it is intended to cover all aspects of the invention as defined by the appended claims.
Claims (10)
1. A catalytic composition for coupling reaction is characterized by comprising a nickel catalyst, a ligand and a cocatalyst, wherein the cocatalyst is halide, and the molar ratio of the nickel catalyst, the ligand and the cocatalyst is 1: 1-3: 30-40, the nickel catalyst exists in one or more of organic matters and inorganic matters, the valence of the nickel is 0 and +2, and the inorganic matters are divalent and non-oxide.
2. The catalytic composition of claim 1, wherein the nickel catalyst is nickel bromide.
3. The catalytic composition of claim 1, wherein the cocatalyst is anhydrous magnesium chloride.
4. The catalytic composition of claim 1 wherein the ligands are nitrogen-containing ligands and phosphine ligands.
5. The catalytic composition of claim 4, wherein the ligand is 4,4 '-dimethoxy-2, 2' -bipyridine with 1, 2-bis (diphenylphosphino) ethane.
6. Use of a catalytic composition according to any one of claims 1 to 5 for the preparation of isoquinoline-1, 3-diones by the steps of: under the action of the catalytic composition and a metal reducing agent, the o-iodoacryloyl benzamide compound and the difluoro compound are subjected to coupling reaction in a solvent to obtain the isoquinoline-1, 3-diketone compound, wherein the reaction route is as shown in formula (I):
in the formula (I), R 1 Is 1 or more substituents of the phenyl ring to which it is attached, each R 1 Independently selected from hydrogen, halogen or methyl; r 2 Is C1-C4 alkyl, phenyl or benzyl; r 3 Is C1-C4 alkyl; r 4 Is morpholine, -N (Et) 2 or-OCH 2 CH 3 。
7. The use of claim 6, wherein the molar ratio of the nickel catalyst, the metal reducing agent and the o-iodoacryloyl benzamide compound is 0.05-0.15: 2-5: 1.
8. The use of claim 6, wherein the molar ratio of the o-iodoacryloyl benzamide compound to the difluoro compound is 1: 1.5-3.
9. Use according to any one of claims 6 to 8, wherein the solvent is at least one of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran, acetonitrile, 1, 4-dioxane and N-methylpyrrolidone.
10. Use according to any one of claims 6 to 8, wherein the metallic reducing agent is manganese powder or zinc powder and the use employs an inert atmosphere.
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| CN108017582A (en) * | 2018-01-29 | 2018-05-11 | 西北师范大学 | A kind of synthetic method of brominated 1,3- isoquinolin derovatives |
| CN110668913A (en) * | 2019-09-16 | 2020-01-10 | 江苏三美化工有限公司 | Preparation method of trifluoroethyl compound |
| WO2022059010A1 (en) * | 2020-09-15 | 2022-03-24 | Yeda Research And Development Co. Ltd. | Alternating current (ac) transition-metal catalysis |
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| CN108017582A (en) * | 2018-01-29 | 2018-05-11 | 西北师范大学 | A kind of synthetic method of brominated 1,3- isoquinolin derovatives |
| CN110668913A (en) * | 2019-09-16 | 2020-01-10 | 江苏三美化工有限公司 | Preparation method of trifluoroethyl compound |
| WO2022059010A1 (en) * | 2020-09-15 | 2022-03-24 | Yeda Research And Development Co. Ltd. | Alternating current (ac) transition-metal catalysis |
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| 周能能等: "可见光催化的高炔丙醇经过1,4芳基迁移实现二氟烷基化反应", 《化学学报》 * |
| 李捷等: "可见光诱导烯烃环化合成二氟烷基化异喹啉二酮", 《应用化学》 * |
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