CN109336934A - Ferrocene bidentate ligand and its application in the asymmetric C-N cross-coupling reaction of copper catalysis - Google Patents
Ferrocene bidentate ligand and its application in the asymmetric C-N cross-coupling reaction of copper catalysis Download PDFInfo
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- CN109336934A CN109336934A CN201811165726.5A CN201811165726A CN109336934A CN 109336934 A CN109336934 A CN 109336934A CN 201811165726 A CN201811165726 A CN 201811165726A CN 109336934 A CN109336934 A CN 109336934A
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- ferrocene
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- bidentate ligand
- asymmetric
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- 239000010949 copper Substances 0.000 title claims abstract description 21
- 239000003446 ligand Substances 0.000 title claims abstract description 20
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 title claims abstract description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 13
- 238000006880 cross-coupling reaction Methods 0.000 title claims abstract description 12
- 238000006555 catalytic reaction Methods 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 13
- 239000011630 iodine Substances 0.000 claims abstract description 13
- 238000004090 dissolution Methods 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims abstract description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 biphenyl compound Chemical class 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical class C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005577 Kumada cross-coupling reaction Methods 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of ferrocene bidentate ligand and its applications in the asymmetric C-N cross-coupling reaction of copper catalysis.Ferrocene bidentate ligand, structural formula are as follows:
Description
Technical field
The invention belongs to metal catalytic fields, and in particular to a kind of ferrocene bidentate ligand designs and its in copper catalysis
Application in asymmetric C-N cross-coupling reaction.
Background technique
Since the 1970s, transition metal-catalyzed cross-coupling reaction (such as Stille reaction, Suzuki reaction,
Kumada reaction and Negishi reaction etc.) it forms C-C key and constructs biphenyl compound and make great progress, some metals
Organic compound (Mg, B, Sn, Zn) and halogenated aromatic compound, which react, can effectively synthesize biphenyl compound, however C-N
The asymmetric building of key, rarely has breakthrough progress all the time, largely constrains asymmetric syntheses C-N class chemical combination
The development process of object.
2012, Cai etc., it was recently reported that the synthetic method of the asymmetric building C-N key of copper catalysis, using BINOL derivative
It as ligand, is complexed from different mantoquitas, successfully prepares in Isosorbide-5-Nitrae-dioxane system and produced with chiral C-N coupling
Object, reaction equation are as follows:
2014, Cai etc. reported similar C-N key coupling reaction using identical catalyst again, provided a kind of new
The method of the asymmetric building tetrahydroquinoline ring of type, achieves preferable catalytic effect, and highest product ee value is 96%, reaction side
Formula is as follows:
Cai etc. is prepared the catalyst system of C-N coupling, is achieved and preferably urged by the rational modification to BINOL skeleton
Change effect, but catalyst preparation process is cumbersome, catalyst price is higher, and reaction temperature is relatively high, these are all limited
The large-scale application of this method.
Summary of the invention
The object of the present invention is to provide a kind of ferrocene bidentate ligands, at the same provide the ligand be catalyzed in copper it is asymmetric
Application in C-N cross-coupling reaction solves how to achieve higher yield and ee value under mild conditions.
Ferrocene bidentate ligand, structural formula are as follows:Wherein R be 2-Me, 3-OMe, 2-t-Bu,
2-F, 2,3,4-F.
Application of the ferrocene bidentate ligand in the asymmetric C-N cross-coupling reaction that copper is catalyzed, comprising the following steps:
Ferrocene bidentate ligand and mantoquita are stirred to coordination in ether, concentration is spin-dried for, and obtains catalyst singly in 10mL stand up reaction bottle
Middle addition 2- benzyl -2- (2- iodine benzyl) malonamide is added acetonitrile dissolution, alkali is then added, the above-mentioned of 5mol% is added and urges
Agent reacts at room temperature 6-12h, directly crosses column after reaction, obtains target product.
The mantoquita is CuI or CuCl or CuBr or Cu (OAc) 2.
The reaction temperature is 20-60 DEG C.
The alkali KOH or NaOH or K2CO3.
The beneficial effects of the present invention are: using ferrocene bidentate compound simple and easy to get as ligand and cheap metal copper
It is coordinated, gained catalyst activity is higher, and cheap, preparation is simple, and reaction condition is mild, without removing water deoxygenation, utilizes
Large-scale application.
Specific embodiment
Embodiment 1
2- benzyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL ethyl alcohol is added, so
35mg KOH is added afterwards, reaction is increased to 50 DEG C, reacts 6h, instead by the catalyst after CuCl and the A1 cooperation of 5mol% is added
It is direct after answering to cross column, obtain white solid product, yield 33%, ee value 82%.
Embodiment 2
2- benzyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL ethyl alcohol is added, so
35mg KOH is added afterwards, reaction is increased to 50 DEG C, reacts 12h, instead by the catalyst after CuCl and the A1 cooperation of 5mol% is added
It is direct after answering to cross column, obtain white solid product, yield 53%, ee value 82%.
Embodiment 3
2- benzyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL ethyl alcohol is added, so
35mg KOH is added afterwards, reaction is increased to 50 DEG C, reacts 12h, instead by the catalyst after CuBr and the A1 cooperation of 5mol% is added
It is direct after answering to cross column, obtain white solid product, yield 64%, ee value 85%.
Embodiment 4
2- benzyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL ethyl alcohol is added, so
35mg KOH is added afterwards, reaction is increased to 50 DEG C, reacts 12h, instead by the catalyst after CuI and the A1 cooperation of 5mol% is added
It is direct after answering to cross column, obtain white solid product, yield 76%, ee value 85%.
Embodiment 5
2- benzyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL ethyl alcohol is added, so
35mg KOH is added afterwards, reaction is increased to 50 DEG C, reaction by the catalyst after Cu (OAc) 2 and the A1 cooperation of 5mol% is added
12h directly crosses column after reaction, obtains white solid product, yield 85%, ee value 89%.
Embodiment 6
2- isopropyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL acetonitrile is added,
Then 35mg NaOH is added, reaction is increased to 60 DEG C, instead by the catalyst after Cu (OAc) 2 and the A2 cooperation of 5mol% is added
9h is answered, column is directly crossed after reaction, obtains white solid product, yield 87%, ee value 91%.
Embodiment 7
2- isopropyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, 2mL acetone solution is added,
Then 35mg KOH is added, reaction is increased to 50 DEG C, reaction by the catalyst after Cu (OAc) 2 and the A3 cooperation of 5mol% is added
6h directly crosses column after reaction, obtains white solid product, yield 94%, and ee value is 93%.
Embodiment 8
2- isopropyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL methanol is added,
Then 35mg NaOH is added, reaction is increased to 30 DEG C, instead by the catalyst after Cu (OAc) 2 and the A4 cooperation of 5mol% is added
12h is answered, directly crosses column after reaction, obtains white solid product, yield 89%, ee value is 84%.
Embodiment 9
2- tert-butyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL acetonitrile is added,
Then 35mg KOH is added, reaction is increased to 30 DEG C, reaction by the catalyst after Cu (OAc) 2 and the A5 cooperation of 5mol% is added
7h directly crosses column after reaction, obtains white solid product, yield 96%, and ee value is 92%.
Embodiment 10
2- tert-butyl -2- (2- iodine benzyl)-malonamide is added in 10mL stand up reaction bottle, the dissolution of 2mL acetonitrile is added,
Then 35mg KOH is added, reaction is increased to 30 DEG C, reaction by the catalyst after Cu (OAc) 2 and the A1 cooperation of 5mol% is added
12h directly crosses column after reaction, obtains white solid product, yield 81%, and ee value is 86%.
Claims (5)
1. ferrocene bidentate ligand, it is characterised in that: structural formula is as follows:Wherein R is 2-Me, 3-
OMe, 2-t-Bu, 2-F, 2,3,4-F.
2. application of the ferrocene bidentate ligand in the asymmetric C-N cross-coupling reaction that copper is catalyzed, it is characterised in that: including
Ferrocene bidentate ligand described in claim 1 and mantoquita: being stirred coordination by following steps in ether, and concentration is spin-dried for, obtains
To catalyst；2- benzyl -2- (2- iodine benzyl) malonamide is added in 10mL stand up reaction bottle, acetonitrile dissolution is added, then
Alkali is added, the above-mentioned catalyst of 5mol% is added, reacts at room temperature 6-12h, directly crosses column after reaction, obtains target product.
3. ferrocene bidentate ligand according to claim 2 is in the asymmetric C-N cross-coupling reaction that copper is catalyzed
Application, it is characterised in that: the mantoquita be CuI or CuCl or CuBr or Cu (OAc) 2.
4. ferrocene bidentate ligand according to claim 2 is in the asymmetric C-N cross-coupling reaction that copper is catalyzed
Application, it is characterised in that: the reaction temperature be 20-60 DEG C.
5. ferrocene bidentate ligand according to claim 2 is in the asymmetric C-N cross-coupling reaction that copper is catalyzed
Application, it is characterised in that: the alkali KOH or NaOH or K2CO3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811165726.5A CN109336934A (en) | 2018-10-08 | 2018-10-08 | Ferrocene bidentate ligand and its application in the asymmetric C-N cross-coupling reaction of copper catalysis |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811165726.5A CN109336934A (en) | 2018-10-08 | 2018-10-08 | Ferrocene bidentate ligand and its application in the asymmetric C-N cross-coupling reaction of copper catalysis |
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| CN109336934A true CN109336934A (en) | 2019-02-15 |
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| CN201811165726.5A Pending CN109336934A (en) | 2018-10-08 | 2018-10-08 | Ferrocene bidentate ligand and its application in the asymmetric C-N cross-coupling reaction of copper catalysis |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113603729A (en) * | 2021-07-08 | 2021-11-05 | 陈熙 | Novel ferrocene bidentate ligand, manganese catalyst, and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107803223A (en) * | 2017-11-23 | 2018-03-16 | 南京工业大学 | Ferrocene cuprous cluster catalyst for catalyzing C-N coupling reaction and preparation method thereof |
| CN108997440A (en) * | 2018-07-09 | 2018-12-14 | 浙江工业大学上虞研究院有限公司 | The method that novel ferrocene bidentate ligand, ligand and mantoquita coordination prepare catalyst |
-
2018
- 2018-10-08 CN CN201811165726.5A patent/CN109336934A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107803223A (en) * | 2017-11-23 | 2018-03-16 | 南京工业大学 | Ferrocene cuprous cluster catalyst for catalyzing C-N coupling reaction and preparation method thereof |
| CN108997440A (en) * | 2018-07-09 | 2018-12-14 | 浙江工业大学上虞研究院有限公司 | The method that novel ferrocene bidentate ligand, ligand and mantoquita coordination prepare catalyst |
Non-Patent Citations (3)
| Title |
|---|
| GANDRATH DAYAKER等，: "Deprotonative metallation of ferrocenes using mixed lithium-zinc and lithium-cadmium combinations", 《CHEM. COMMUN.》 * |
| JIANGUANG LIU等，: "An Enantioselective Synthesis of Spirobilactams through Copper-Catalyzed Intramolecular Double N-Arylationand Phase Separation", 《ANGEW.CHEM.INT.ED.》 * |
| NIAN HE等，: "Copper-Catalyzed Enantioselective Intramolecular Aryl C-N Coupling: Synthesis of Enantioenriched 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides via an Asymmetric Desymmetrization Strategy", 《ORG. LETT.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113603729A (en) * | 2021-07-08 | 2021-11-05 | 陈熙 | Novel ferrocene bidentate ligand, manganese catalyst, and preparation method and application thereof |
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