CN108947896B - Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative - Google Patents
Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative Download PDFInfo
- Publication number
- CN108947896B CN108947896B CN201811155413.1A CN201811155413A CN108947896B CN 108947896 B CN108947896 B CN 108947896B CN 201811155413 A CN201811155413 A CN 201811155413A CN 108947896 B CN108947896 B CN 108947896B
- Authority
- CN
- China
- Prior art keywords
- aryl
- pyridyl
- alpha
- acetate
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a method for synthesizing a-aryl-a- (5-pyridyl) acetate derivatives, which comprises the following steps: dissolving pyridine derivatives and phenyl diazo ester in a solvent, and reacting at 60-120 ℃ in the presence of a catalyst and an additive to generate a-aryl-a- (5-pyridyl) acetate derivatives; the molar ratio of the 2-pyrrolidinyl pyridine to the methyl phenyl diazoacetate is 1:1-1: 6. The method is simple, convenient and efficient, and has high regioselectivity. The used raw materials are cheap and easy to obtain, and the preparation method is not sensitive to air. In addition, the whole experimental operation process is simple and easy to implement, the steps are simple and convenient, and the product is easy to purify.
Description
Technical Field
The invention relates to the field of pyridine structure derivatives, in particular to a synthetic method of an alpha-aryl-alpha- (5-pyridyl) acetate derivative.
Technical Field
Pyridine structures are ubiquitous in biologically active and drug molecules. It becomes very important to achieve the conversion of the C-H bond at different sites of the pyridine. In order to realize the diversification of the pyridine structure, previous reports all focus on the C2 and C4 positions of pyridine, and the reactive transformation is realized by using an active catalyst and a guide group. But the C-H bond at the C3 position of pyridine is difficult to activate without the aid of auxiliary tools. Only the subject group such as Yujinquan reports the coupling reaction of the C3 position of pyridine with olefin, halogenated aromatic hydrocarbon, aldehyde and hydrosilane. Therefore, diversified catalytic systems are developed, and the coupling reaction of the pyridine C3 position and different coupling reagents is still very urgent.
The methods for functionalizing C-H bond on pyridine reported at present mainly include: one is to use active catalysts and directing groups to effect the conversion at the C2 and C4 positions of the pyridine. Such as (1) Lewis, J.C.; bergman, r.g.; ellman, J.A.A. A. vacuum Biaryl phosphorus Acid-Catalyzed Reduction of alpha-Imino Esters The high antibiotic selectivity of alpha-Amino Esters [ J ] J.Am.chem.Soc.2007,129, 5332; (2) andou, t.; saga, y.; komai, h.; matsunaga, s.; kanai, m.cobalt-catalyst C4-Selective direction alteration of pyrimidines. [ J ] antenna. chem., int.ed.2013,52,3213; (3) zhu, c.j.; oliveira, j.c.a.; shen, z.g.; huang, h.w.; ackermann, L.Manganise (II/III/I) -catalysis C-H Arylations in contacts Flow. [ J ] ACS Catal.2018,8,4402.; (4) cho, s.h.; hwang, s.j.; chang, S.Palladium-Catalyzed C-H function of Pyridine N-Oxides: high Selective alkylation and Direct alkylation with unreacted olefins [ J ] J.am.chem.Soc.2008,130,9254.
The second is coupling reaction between pyridine C3 and olefin, aryl halide, aldehyde and hydrosilane. Such as (1) Ye, m.c.; gao, g.l.; yu, J.Q.ligand-protein C-3 Selective C-H introduction of pyrimidines with Pd catalysis [ J]J.Am.Chem.Soc.2011,133,6964；(2)Li,B.J.；Shi,Z.J.Ir-catalyzed highly selective addition of pyridyl C–H bonds to aldehydes promoted by triethylsilane.[J]Chem.Sci.2011,2,488；(3)
S.；Oestreich,M.Catalytic Electrophilic C-H Silylation of Pyridines Enabled by Temporary Dearomatization.[J]Angew.Chem.,Int.Ed.2015,54,15876。
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a simple and efficient method for synthesizing the alpha-aryl-alpha- (5-pyridyl) acetate ester derivative, the raw materials used by the method are cheap and easy to obtain, and the whole operation process is simple and easy to implement.
The purpose of the invention is realized by the following technical scheme.
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
dissolving pyridine derivatives and phenyl diazo ester in a solvent, and reacting at 60-120 ℃ in the presence of a catalyst and an additive to generate alpha-aryl-alpha- (5-pyridyl) acetate derivatives;
the pyridine derivative has a structure shown as a formula A, the phenyl diazo ester has a structure shown as a formula B, and the alpha-aryl-alpha- (5-pyridyl) acetate derivative has a structure shown as a formula C:
in the formulae A and C, R1Is one of pyrrolidinyl, piperidinyl, morpholinyl, indolinyl, tetrahydroisoquinolinyl, N-dimethylamino; in the formulae A and C, R2Is one of 3-Me, 4-Me, 6-Me, 3-MeO, 3-Cl, 3-Br, 3-CN, 3-Ph, 3-phenylethynyl and 3-styryl; in the formulae B and C, R3Is 4-Me, 4-tBu, 4-F, 4-Cl, 4-Br, 3-Br, 2-Br and 4-Ph.
The pyridine formula A has been reported in the literature (Ahneman, D.T.; Doyle, A.G.C-H catalysis of amines with aryl halides by nitrile-phosphorus catalysis [ J ] chem.Sci.2016,7,7002)
Preferably, the molar ratio of the pyridine derivative to the phenyl diazo ester is 1:1 to 1: 6.
Further preferably, the molar ratio of the pyridine derivative to the phenyl diazo ester is 1: 3.
Preferably, the solvent is trifluoroethanol.
Preferably, the catalyst is one or more of cobalt (II) acetylacetonate, cobalt acetate, cobalt chloride, cobalt bromide, palladium acetate, dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer and dichloro (pentamethylcyclopentadienyl) iridium (III) dimer.
Further preferably, the catalyst is cobalt bromide.
Preferably, the catalyst is used in an amount of 5 to 10% by mole based on the pyridine derivative.
Preferably, the additive is copper acetate, zinc acetate, ferrous sulfate or silver hexafluoroantimonate, and more preferably is copper acetate.
Preferably, the reaction time is 8-24 h.
Further preferably, the reaction time is 12 h.
Preferably, after the reaction is finished, separating and purifying the product by adopting column chromatography; the eluent of the column chromatography is a mixed solvent of petroleum ether and acetone.
Compared with the prior art, the invention has the following effects and advantages:
the method is simple, convenient and efficient, has high regioselectivity, uses simple and easily-obtained raw materials, and is insensitive to air. In addition, the whole operation process is simple and easy to implement, the steps are simple and convenient, and the product is easy to purify.
Drawings
Figure 1 is a hydrogen spectrum of compound 1.
Figure 2 is a carbon spectrum of compound 1.
Fig. 3 is a hydrogen spectrum of compound 2.
Figure 4 is a carbon spectrum of compound 2.
Fig. 5 is a hydrogen spectrum of compound 3.
Figure 6 is a carbon spectrum of compound 3.
FIG. 7 is a hydrogen spectrum of Compound 4.
Figure 8 is a carbon spectrum of compound 4.
Fig. 9 is a hydrogen spectrum of compound 5.
Figure 10 is the carbon spectrum of compound 5.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
Example 1
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
(1) 2-pyrrolidinylpyridine (29.6mg, 0.2mmol), methyl phenyldiazoacetate (105.6mg, 0.3mmol), cobalt bromide (2.2mg, 5% mmol), copper acetate (3.6mg, 10% mmol), and trifluoroethanol (2mL) were added to a sealed tube, and the mixture was stirred at 60 ℃ for 12 hours. After the reaction is finished, cooling the reaction system to room temperature, filtering, spin-drying, and further separating and purifying by column chromatography to obtain 46.7mg of a product, wherein the yield is as follows: 79 percent.
The structural characterization data of the product obtained in this example are as follows:
1H NMR(400MHz,CDCl3) δ 8.08(s,1H),7.45(d, J ═ 8.5Hz,1H), 7.35-7.24 (m,5H),6.34(d, J ═ 8.8Hz,1H),4.90(s,1H),3.74(s,3H), 3.50-3.40 (m,4H), 2.04-1.95 (m,4H). the hydrogen spectrum is shown in fig. 1.
13C NMR(101MHz,CDCl3) Delta 173.2,156.6,147.9,138.9,137.3,128.6,128.2,127.2,121.2,106.5,53.8,52.3,46.7 and 25.6. the carbon spectrum is shown in figure 2.
High Resolution MS: calculated value C18H21N2O2[M+H]+297.1598, found 297.1568.
The structure of the resulting product was deduced from the above data as follows:
example 2
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
(1) 2-indolinylpyridine (39.2mg, 0.2mmol), methyl phenyldiazoacetate (70.4mg, 0.4mmol), cobalt bromide (2.2mg, 5% mmol), copper acetate (3.6mg, 10% mmol), and trifluoroethanol (2mL) were added to a sealed tube, and the mixture was stirred at 80 ℃ for 12 hours. After the reaction is finished, cooling the reaction system to room temperature, filtering, spin-drying, and further separating and purifying by column chromatography to obtain 30.3mg of a product, wherein the yield is as follows: 44 percent.
The structural characterization data of the product obtained in this example are as follows:
1H NMR(400MHz,CDCl3) δ 8.36(d, J ═ 4.2Hz,1H),8.17(d, J ═ 8.2Hz,1H),7.59(t, J ═ 7.8Hz,1H),7.36(d, J ═ 3.1Hz,4H), 7.32-7.26 (m,2H), 7.20-7.15 (m,1H),6.78(t, J ═ 8.2Hz,2H),5.03(s,1H),4.05(t, J ═ 8.5Hz,2H),3.78(s,3H),3.20(t, J ═ 8.5Hz,2H), hydrogen spectrum fig. 3.
13C NMR(101MHz,CDCl3) Delta 173.4,155.4,148.0,144.3,139.3,137.3,132.0,130.6,128.5,127.7,127.1,124.8,114.5,113.3,108.6,56.5,52.2,49.6 and 27.7. the carbon spectrum is shown in figure 4.
High Resolution MS: calculated value C22H21N2O2[M+H]+345.1598, found 345.1601.
The structure of the resulting product was deduced from the above data as follows:
example 3
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
(1) 4-methyl-2-pyrrolidinylpyridine (32.4mg, 0.2mmol), methyl phenyldiazoacetate (123.2mg, 0.7mmol), cobalt bromide (2.2mg, 5% mmol), copper acetate (3.6mg, 10% mmol), and trifluoroethanol (2mL) were added to a sealed tube, and the mixture was stirred at 90 ℃ for 12 h. After the reaction is finished, cooling the reaction system to room temperature, filtering, spin-drying, and further separating and purifying by column chromatography to obtain 38.4mg of a product, wherein the yield is as follows: 62 percent.
The structural characterization data of the product obtained in this example are as follows:
1H NMR(400MHz,CDCl3) δ 7.85(s,1H), 7.25-7.13 (m,5H),6.10(s,1H),4.96(s,1H),3.65(s,3H), 3.40-3.31 (m,4H),2.07(s,3H), 1.94-1.87 (m,4H). Hydrogen spectrum is shown in FIG. 5.
13C NMR(100MHz,CDCl3) Delta 173.2,156.7,147.6,146.5,138.0,128.8,128.5,127.2,120.8,107.7,52.3,51.6,46.6,25.6,19.8. the carbon spectrum is shown in figure 6.
High Resolution MS：C17H23N2O2Calculated value [ M + H]+311.1754, found 311.176]The structure of the resulting product was deduced from the above data as follows:
example 4
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
(1) 3-Phenylethynyl-2-pyrrolidinopyridine (49.6mg, 0.2mmol), methyl phenyldiazoacetate (17.6mg, 0.1mmol), cobalt bromide (2.2mg, 5% mmol), copper acetate (3.6mg, 10% mmol), and trifluoroethanol (2mL) were added to a sealed tube, and the mixture was stirred at 100 ℃ for 12 h. After the reaction is finished, cooling the reaction system to room temperature, filtering, spin-drying, and further separating and purifying by column chromatography to obtain 29.3mg of a product, wherein the yield is as follows: 37 percent.
The structural characterization data of the product obtained in this example are as follows:
1H NMR(400MHz,CDCl3) δ 8.05(d, J ═ 2.3Hz,1H),7.66(d, J ═ 2.3Hz,1H), 7.50-7.45 (m,2H), 7.39-7.33 (m,7H), 7.32-7.28 (m,1H),4.91(s,1H),3.86(t, J ═ 6.5Hz,4H),3.78(s,3H), 2.00-1.95 (m,4H) hydrogen spectrum see fig. 7.
13C NMR(101MHz,CDCl3) Delta 172.8,157.0,147.5,142.9,138.4,130.8,128.8,128.4,128.3,128.1,127.4,123.7,121.9,103.0,93.2,88.7,53.5,52.4,49.3,25.8. the carbon spectrum is shown in figure 8.
High Resolution MS：C26H25N2O2Calculated value [ M + H]+397.1911, found 397.1912.
The structure of the resulting product was deduced from the above data as follows:
example 5
A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
(1) in a sealed tube, 2-pyrrolidinylpyridine (29.6mg, 0.2mmol), methyl 4-tert-butylanilinoacetate (278.4mg, 1.2mmol), cobalt bromide (2.2mg, 5% mmol), copper acetate (3.6mg, 10% mmol), trifluoroethanol (2mL) and the mixture was stirred at 120 ℃ for 12 h. After the reaction is finished, cooling the reaction system to room temperature, filtering, spin-drying, and further separating and purifying by column chromatography to obtain 44.5mg of a product, wherein the yield is as follows: 66 percent.
The structural characterization data of the product obtained in this example are as follows:
1H NMR(400MHz,CDCl3) δ 8.09-8.06 (m,1H), 7.51-7.46 (m,1H),7.34(d, J ═ 8.0Hz,2H),7.24(d, J ═ 7.9Hz,2H),6.35(d, J ═ 8.8Hz,1H),4.88(s,1H),3.75(s,3H),3.45(t, J ═ 6.0Hz,4H), 2.05-1.97 (m,5H),1.31(s,9H) hydrogen spectrum see fig. 9.
13C NMR(101MHz,CDCl3) Delta 173.3,156.6,150.0,147.9,137.4,135.8,127.9,125.6,121.5,106.5,53.4,52.2,46.7,34.4,31.3,25.5. the carbon spectrum is shown in figure 10.
High Resolution MS：C22H29N2O2Calculated value [ M + H]+353.2224, found 353.2198.
The structure of the resulting product was deduced from the above data as follows:
the above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (5)
1. A method for synthesizing an α -aryl- α - (5-pyridyl) acetate derivative, comprising the steps of:
dissolving pyridine derivatives and phenyl diazo ester in a solvent, and reacting at 60-120 ℃ in the presence of a catalyst and an additive to generate alpha-aryl-alpha- (5-pyridyl) acetate derivatives;
the pyridine derivative has a structure shown as a formula A, the phenyl diazo ester has a structure shown as a formula B, and the alpha-aryl-alpha- (5-pyridyl) acetate derivative has a structure shown as a formula C:
in the formulae A and C, R1Is one of pyrrolidinyl, piperidinyl, morpholinyl, indolinyl, tetrahydroisoquinolinyl, N-dimethylamino; in the formulae A and C, R2Is one of 3-Me, 4-Me, 6-Me, 3-MeO, 3-Cl, 3-Br, 3-CN, 3-Ph, 3-phenylethynyl and 3-styryl; in the formulae B and C, R3Is 4-Me, 4-tOne of Bu, 4-F, 4-Cl, 4-Br, 3-Br, 2-Br and 4-Ph;
the catalyst is one or more of cobalt acetate, cobalt chloride and cobalt bromide;
the solvent is trifluoroethanol;
the additive is copper acetate.
2. The method for synthesizing α -aryl- α - (5-pyridyl) acetate derivative according to claim 1, wherein the molar ratio of the pyridine derivative to the phenyldiazo ester is 1:1 to 1: 6.
3. The method of claim 2, wherein the molar ratio of the pyridine derivative to the phenyldiazo ester is 1: 3.
4. The method of claim 1, wherein the catalyst is used in an amount of 5 to 10% by mole based on the pyridine derivative.
5. The method for synthesizing α -aryl- α - (5-pyridyl) acetate derivatives according to claim 1, wherein the reaction time is 8 to 24 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811155413.1A CN108947896B (en) | 2018-09-30 | 2018-09-30 | Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811155413.1A CN108947896B (en) | 2018-09-30 | 2018-09-30 | Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108947896A CN108947896A (en) | 2018-12-07 |
| CN108947896B true CN108947896B (en) | 2021-09-21 |
Family
ID=64472712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811155413.1A Active CN108947896B (en) | 2018-09-30 | 2018-09-30 | Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108947896B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113291A (en) * | 2013-02-04 | 2013-05-22 | 浙江大学 | Synthesis method of 3-position alkenyl pyridine derivatives |
| CN103936537A (en) * | 2014-04-24 | 2014-07-23 | 华东师范大学 | Method for performing gold-catalyzed selective C-H bond functionalization on phenol and aniline |
| CN108395412A (en) * | 2018-04-25 | 2018-08-14 | 浙江大学 | A kind of triazole derivatives and preparation method thereof |
-
2018
- 2018-09-30 CN CN201811155413.1A patent/CN108947896B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113291A (en) * | 2013-02-04 | 2013-05-22 | 浙江大学 | Synthesis method of 3-position alkenyl pyridine derivatives |
| CN103936537A (en) * | 2014-04-24 | 2014-07-23 | 华东师范大学 | Method for performing gold-catalyzed selective C-H bond functionalization on phenol and aniline |
| CN108395412A (en) * | 2018-04-25 | 2018-08-14 | 浙江大学 | A kind of triazole derivatives and preparation method thereof |
Non-Patent Citations (7)
| Title |
|---|
| Copper(II)–acid co-catalyzed intermolecular substitution of electron-rich aromatics with diazoesters;Eiji Tayama et al.;《Tetrahedron Letters》;20120722;第53卷;第5159-5161页 * |
| Cp*Co(III)-catalysed selective alkylation of C-H bonds of arenes and heteroarenes with α-diazocarbonyl compounds;Jayanta Ghorai et al.;《Organic & Biomolecular Chemistry》;20180921;第16卷(第40期);第7346-7350页 * |
| CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds;José M. Fraile et al.;《Org. Biomol. Chem.》;20130415;第11卷;第4327-4332页 * |
| Hui Liu et al..Mechanistic Insights into Asymmetric C −H Insertion Cooperatively Catalyzed by a Dirhodium(II) Complex and Chiral Phosphoric Acid.《Organometallics》.2016,第35卷第2003-2009页. * |
| Iron-Catalyzed C-H Fuctionalization of Indoles;Yan Cai et al.;《Adv. Synth. Catal.》;20111107;第353卷;第2939-2944页 * |
| Ying Xia et al..Rh(I)-Catalyzed Cross-Coupling of α‑Diazoesters with Arylsiloxanes.《Org. Lett.》.2015,第17卷第956-959页. * |
| 过渡金属催化重氮化合物参与的芳烃碳(sp2)-氢键官能团化研究进展;刘路 张俊良;《Chin. J. Org. Chem.》;20170525;第37卷;第1117-1126页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108947896A (en) | 2018-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110563535B (en) | Method for synthesizing 1, 2-disubstituted olefin compound by alkyne alkylation | |
| Shen et al. | Synthesis of polyfluoroarene-substituted benzofuran derivatives via cooperative Pd/Cu catalysis | |
| Wang et al. | Palladium-catalyzed α-regioselective allylic amination of Morita–Baylis–Hillman acetates with simple aromatic amines | |
| CN109516946B (en) | Method for preparing carbazole compound | |
| Tang et al. | Efficient palladium-catalyzed cross-coupling reaction of alkynyl halides with organoboronic acids under aerobic conditions | |
| JP6168044B2 (en) | Method for producing tetrahydrofuran compound | |
| Kojima et al. | Tandem Suzuki cross-coupling-Heck reactions | |
| CN108947896B (en) | Synthetic method of alpha-aryl-alpha- (5-pyridyl) acetate derivative | |
| Wang et al. | Rh-catalyzed alkoxycarbonylation of unactivated alkyl chlorides | |
| KR102207333B1 (en) | Novel Production Method for Quadruple Cyclic Compounds | |
| CN115260080B (en) | Preparation method of indole-3-formamide compound | |
| Ballini et al. | Potassium Fluoride/Basic Alumina as Far Superior Heterogeneous Catalyst for the Chemoselective Conjugate Addition of Nitroalkanes to Electron‐Poor Alkenes Having Two Electron‐Withdrawing Groups in α‐and β‐Positions | |
| CN113121421B (en) | Synthesis method of chiral beta-aryl substituted carboxylic acid derivative | |
| Zhang et al. | Palladium-catalyzed and norbornene-mediated C–H amination and C–O alkenylation of aryl triflates | |
| US20020016512A1 (en) | Heterogeneously catalyzed process for cross coupling aryl chlorides with aryl boronic acids | |
| CN111484436A (en) | Method for introducing isopentenyl group to C3 position of indole | |
| WO2023084534A1 (en) | Pincer–based cobalt catalysts for hydrogenation reaction and its process of preparation thereof | |
| Di Nicola et al. | Hydrotalcite-supported palladium nanoparticles as catalysts for the hydroarylation of carbon–carbon multiple bonds | |
| CN116063232B (en) | Spiro-bisindane ligand and preparation method and application thereof | |
| Maligres et al. | Synthesis of Fused Oxepane HIV Integrase Inhibitor MK-1376 | |
| CN115057808B (en) | Synthesis method of Z-3-vinyl substituted isoindolinone compound | |
| CN109824567B (en) | Synthetic method of aromatic aldehyde | |
| CN112239456B (en) | Preparation method of substituted 2, 3-dihydroquinolone compound | |
| CN110357879B (en) | Preparation method of C-3 benzyl indolizine compound | |
| CN110003062B (en) | N-phenyl-N-p-toluenesulfonyl difluoroacetamide and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |