CN109776617B - A kind of acetone coordination binuclear palladium compound and preparation method and application thereof - Google Patents
A kind of acetone coordination binuclear palladium compound and preparation method and application thereof Download PDFInfo
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 150000002941 palladium compounds Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims abstract description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 15
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- CVZIHXRHSDYALS-UHFFFAOYSA-N 1-fluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)CF CVZIHXRHSDYALS-UHFFFAOYSA-N 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 230000008878 coupling Effects 0.000 abstract description 5
- 238000010168 coupling process Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 abstract description 3
- LELFVORHOKZNGY-UHFFFAOYSA-N 3-fluoropentane-2,4-dione Chemical compound CC(=O)C(F)C(C)=O LELFVORHOKZNGY-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002146 bilateral effect Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- -1 chloromethyl CCl3 Chemical compound 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 2
- KBVDUUXRXJTAJC-UHFFFAOYSA-N 2,5-dibromothiophene Chemical compound BrC1=CC=C(Br)S1 KBVDUUXRXJTAJC-UHFFFAOYSA-N 0.000 description 2
- QBKFSWPZWWKKMJ-UHFFFAOYSA-N 4,7-dibromo-1,2,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=C1N=NS2 QBKFSWPZWWKKMJ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 2
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses an acetone coordination binuclear palladium compound and a preparation method and application thereof. The preparation method of the acetone coordination palladium compound comprises the following steps: with (fluoro) acetylacetone (HF)xacac) and palladium chloride are used as raw materials to synthesize a compound which takes acetone as a bridge to link two palladium atoms under the condition of mixed liquid of aromatic hydrocarbon and acetone, and the structure is shown as follows. Compared with the prior art, the palladium compound with a brand-new structure is prepared; all the products for catalyzing the Sonogashira coupling reaction are bilateral coupling products, the unilateral coupling products are almost not generated, the excellent reaction activity is shown, the method has better industrialization prospect,
Description
Technical Field
The invention relates to a palladium compound with a new structure, preparation and application thereof, in particular to a compound with two palladium atoms linked by an acetone bridge, a preparation method thereof, and a specific catalytic activity in Sonogashira coupling reaction, belonging to the field of chemistry and chemical engineering.
Background
The coupling reaction is an important reaction for preparing organic photoelectric materials and common important drugs at present, the used catalyst is an organic compound of palladium, and the palladium-based molecular catalyst has the best effect and the most extensive application on the common coupling reaction and is one of the most important industrial catalysts.
Through the development of the palladium-based molecular coupling catalyst for nearly 20 years, a plurality of catalysts are successively proposed: including Pd (F)3acac)2、Pd(F6acac)2、 Pdx(dba)y、Pd(acac)2Etc., Stefano Nicolai et al Pd (hfacac)2Oxyalkynylation of a coupling iodide and an olefin, and the like. However, with the increasing demand of human beings for new organic photoelectric materials and new drugs, the original catalyst cannot meet the demand, and a palladium-based molecular coupling catalyst with a new structure needs to be developed to achieve the purposes of high catalytic activity and high selectivity. Fukuda reported that new methylene-coordinated palladium compounds are of interest to various researchers, but the synthetic method would use highly toxic mercury salts; efimenko et al use similar novel compounds from Fukuda and found that methylene-coordinated palladium atoms enhance catalyst activity.
Disclosure of Invention
The invention aims to overcome the defects reported in the prior art and provide a high-activity acetone coordination binuclear palladium compound with a brand-new structure and a preparation method and application thereof, and the compound has higher bilateral selectivity on a product of Sonogashira coupling reaction between 2, 5-dibromothiophene and methylbutynol and between 4, 7-dibromobenzothiadiazole and methylbutynol.
The purpose of the invention can be realized by the following technical scheme:
the molecular structure of the acetone coordination binuclear palladium compound is as follows:
r in the above molecular structure represents a fluoromethyl group CF3、CHF2、CH2F; r' represents hydrogen, C1～C10A straight-chain or branched alkyl group of (1). The mechanism of formation of the acetone coordinated binuclear palladium compound is as follows:
the preparation method comprises the steps of mixing (fluoro) acetylacetone (HF)xacac) and palladium chloride are used as raw materials to synthesize a compound which takes acetone as a bridge to link two palladium atoms under the condition of a mixed solution of aromatic hydrocarbon and acetone.
The method comprises the following specific steps: under the protection of nitrogen, Pd (F)xacac)2Adding sodium bicarbonate solid into the mixture solution of acetone and toluene in a ratio of 1:1, adjusting the reaction system to be alkalescent, and carrying out reflux reaction for 12 hours to obtain the target compound.
Two acetone molecules are used as ligands, and the oxygen and methylene of the carbonyl group respectively bridge two palladium atoms to form an octa-ring.
R represents fluoromethyl CF3、CHF2、CH2F and chloromethyl CCl3、CHCl2、CH2Cl, and the like.
R' represents hydrogen, C1～C10Linear or branched alkyl.
The acetone activated palladium catalyst improves the catalytic activity of the acetone activated palladium catalyst, and has important significance in improving the original catalyst and inventing a palladium compound with a brand new structure under the industrial application of the contemporary coupling reaction and the trend of relying on the efficient catalyst.
Detailed Description
Example 1.77g (0.01mol) of palladium chloride was weighed out and dissolved in 20mL of 0.3mol/L diluted hydrochloric acid, 3.1mL (3.00g) of acetylacetone was added slowly with continuous stirring, the reaction was stirred at 70 ℃ for 1 hour, a solution of 0.8g of sodium hydroxide dissolved in 40mL of distilled water was added continuously, the reaction was stirred continuously for 5 hours, the mixture was left to stand, filtered, washed with water until no chloride ion was detected in the washing solution, and dried at 50 ℃ for 8 hours to obtain a pale yellow palladium acetylacetonate solid. The palladium acetylacetonate thus obtained was added to 50mL of a 1:1 mixture of acetone and toluene, and 0.05g of a solid sodium bicarbonate was added to react under nitrogen for 10 hours, followed by filtration to obtain a filtrate, which was concentrated to dryness and dried at 50 ℃ for 1 hour to obtain a dark red granular solid (2.01 g, 38.35% yield). (Pd-1)
Characteristic structure parameters:<1>elemental analysis: found C36.64%, H4.58%, Pd 40.46%;<2>mass spectrum: MS (EI)+) m/z:524，[MH]+；<3>1H-NMR(400Hz,DMSO):δ5.0ppm(2H,CH)；2.6ppm(4H,CH2)； 2.1ppm(6H,CH3)；1.95ppm(12H,CH3) And C16H24O6Pd2The structural data of (a) is substantially consistent.
Example 2 1.77g (0.01mol) of palladium chloride was weighed out and dissolved in 20mL of 0.3mol/L diluted hydrochloric acid, 3.6mL (4.62g) of trifluoroacetylacetone was slowly added with continuous stirring, the reaction was stirred at 70 ℃ for 1 hour, a solution of 0.8g of sodium hydroxide in 40mL of distilled water was further added, the reaction was further stirred for 5 hours, the mixture was left to stand, filtered, washed with water until no chloride ion was detected in the washing solution, and dried at 50 ℃ for 8 hours to obtain a pale yellow palladium trifluoroacetylacetone solid. The palladium trifluoroacetylacetonate obtained was added to 50mL of a 1:1 mixture of acetone and toluene, 0.05g of a solid sodium bicarbonate was added, the reaction was carried out for 10 hours under nitrogen protection, filtration was carried out, the filtrate was taken, concentrated to dryness and dried at 50 ℃ for 1 hour, and 3.15 g of a dark red granular solid was obtained in 49.84% yield. (Pd-2)
Characteristic structure parameters:<1>elemental analysis: found C30.38%, H2.85%, F10.84%, Pd 33.54%;<2>mass spectrum: MS (EI)+)m/z:631，[MH]+；<3>1H-NMR(400Hz,DMSO):δ5.2ppm(2H,CH)；2.7ppm(4H,CH2)； 2.1ppm(6H,CH3)；1.98ppm(6H,CH3) And C16H18F3O6Pd2The structural data of (a) is substantially consistent.
Example 3 1.77g (0.01mol) of palladium chloride was weighed out and dissolved in 20mL of 0.3mol/L diluted hydrochloric acid, 4.24mL (6.24g) of hexafluoroacetylacetone was slowly added with continuous stirring, the reaction was stirred at 70 ℃ for 1 hour, a solution of 0.8g of sodium hydroxide in 40mL of distilled water was further added, the reaction was further stirred for 5 hours, the mixture was left to stand, filtered, washed with water until no chloride ion was detected in the washing solution, and dried at 50 ℃ for 8 hours to obtain a pale yellow palladium hexafluoroacetylacetone solid. The resulting palladium hexafluoroacetylacetonate was added to 50mL of a 1:1 mixture of acetone and toluene, 0.05g of a solid sodium bicarbonate was added, the mixture was reacted for 10 hours under nitrogen, filtered, the filtrate was concentrated to dryness and dried at 50 ℃ for 1 hour to give 4.72g of a dark red granular solid, with a yield of 63.78%. (Pd-3)
Characteristic structure parameters:<1>elemental analysis: found C25.95%, H2.43%, F15.41%, Pd 28.65%;<2>mass spectrum: MS (EI)+)m/z:740，[MH]+；<3>1H-NMR(400Hz,DMSO):δ5.4ppm(2H,CH)；2.6ppm(4H,CH2)； 2.1ppm(6H,CH3) And C16H18F6O6Pd2The structural data of (a) is substantially consistent.
Example 42, 5-dibromothiophene (1.0equiv.), methylbutynol (3equiv.), catalyst (5 mol% vs. 2, 5-dibromothiophene): pd-1, Pd-2, Pd-3, Pd (PPh)3)4As a control in Et3A mixture of THF and THF (1: 1) (10mL) was reacted at 25 ℃ for 12 h.
Of Compound A1H NMR(400MHz,CDCl3):δ(ppm)7.02(d,1H,J＝6.2Hz),6.92(d,1H,J＝6.2 Hz),2.30(bs,1H；2OH),1.62(s,6H；2CH3) (ii) a Of compounds B1H NMR(400MHz,CDCl3):δ(ppm) 6.99(s,2H；2ArH),2.24(bs,2H；2OH),1.60(s,12H；4CH3).
Example 54, 7-Dibromobenzothiadiazole (1.0equiv.), methylbutynol (3equiv.), Pd catalyst (5 mol% relative to 4, 7-dibromobenzothiadiazole) Pd-1, Pd-2, Pd-3, Pd (PPh)3)4As a control in Et3A mixture of THF and THF (1: 1) (10mL) was reacted at 25 ℃ for 12 hours.
Of Compound A1H NMR(400MHz,CDCl3),δ(ppm)＝7.80-7.76(d,1H,J＝7.6Hz,ArH), 7.57-7.55(d,1H,J＝7.6Hz,ArH),1.71(s,6H,2CH3) (ii) a Of compounds B1H NMR(CDCl3,400MHz): δ(ppm)＝7.61(s,2H,2ArH),3.09(bs,2H,2OH),1.71(s,12H,4CH3).
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003043735A2 (en) * | 2001-11-23 | 2003-05-30 | Degussa Ag | Aromatic compounds containing nitrogen and p-functionalized amines, the production thereof and their use in catalytic reactions |
| CN101143907A (en) * | 2007-11-01 | 2008-03-19 | 复旦大学 | A kind of binuclear nickel, copper olefin polymerization catalyst and its preparation method and application |
| CN101184711A (en) * | 2005-05-27 | 2008-05-21 | 普罗梅鲁斯有限责任公司 | Nucleophilic heterocyclic carbene derivatives of pd(acac)2 for cross-coupling reactions |
| CN108752179A (en) * | 2018-07-16 | 2018-11-06 | 扬州工业职业技术学院 | A kind of preparation method and applications of dimethylacetamide acetone gold |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003043735A2 (en) * | 2001-11-23 | 2003-05-30 | Degussa Ag | Aromatic compounds containing nitrogen and p-functionalized amines, the production thereof and their use in catalytic reactions |
| CN101184711A (en) * | 2005-05-27 | 2008-05-21 | 普罗梅鲁斯有限责任公司 | Nucleophilic heterocyclic carbene derivatives of pd(acac)2 for cross-coupling reactions |
| CN101143907A (en) * | 2007-11-01 | 2008-03-19 | 复旦大学 | A kind of binuclear nickel, copper olefin polymerization catalyst and its preparation method and application |
| CN108752179A (en) * | 2018-07-16 | 2018-11-06 | 扬州工业职业技术学院 | A kind of preparation method and applications of dimethylacetamide acetone gold |
Non-Patent Citations (4)
| Title |
|---|
| Organo Palladium(II) Complexes with PdC4 Coordination: Phenylethinyl- and Methylphenylethinyl complexes;Dirk Walther 等;《Z.Anorg.Allg.Chem.》;20081212;第635卷;第1187-1195页 * |
| Regioselective olefin arylation catalyzed by [Ir(acac)2Cl]2 with base;Takaya Matsumoto 等;《Inorganic Chemistry Communications》;20021231;第5卷;第105-106页 * |
| Sonogashira 偶联反应的过渡金属催化剂研究进展;阚文涛 等;《化工进展》;20131231;第32卷(第4期);第804-808,823页 * |
| Synthesis, Structure, and Reactivity of O-Donor Ir(III) Complexes: C-H Activation Studies with Benzene;Gaurav Bhalla 等;《J. AM. CHEM. SOC.》;20050723;第127卷;第11372-11389页 * |
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