CN110041374A - 一种钯配合物的制备方法 - Google Patents
一种钯配合物的制备方法 Download PDFInfo
- Publication number
- CN110041374A CN110041374A CN201910375471.3A CN201910375471A CN110041374A CN 110041374 A CN110041374 A CN 110041374A CN 201910375471 A CN201910375471 A CN 201910375471A CN 110041374 A CN110041374 A CN 110041374A
- Authority
- CN
- China
- Prior art keywords
- palladium
- palladium complex
- preparation
- solution
- triphenylphosphine
- 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.)
- Pending
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 53
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000013078 crystal Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 3
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 238000002604 ultrasonography Methods 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 230000003321 amplification Effects 0.000 abstract description 3
- 238000006880 cross-coupling reaction Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- GJOGRUGECVQJBK-UHFFFAOYSA-N 2-diphenylphosphanylacetic acid Chemical compound C=1C=CC=CC=1P(CC(=O)O)C1=CC=CC=C1 GJOGRUGECVQJBK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PRMGWNQIQKIHLT-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)P(C1=CC=CC=C1)CC(=O)O Chemical compound [Na].C1(=CC=CC=C1)P(C1=CC=CC=C1)CC(=O)O PRMGWNQIQKIHLT-UHFFFAOYSA-N 0.000 description 2
- ZOQCZTRFTARYGJ-UHFFFAOYSA-N chlorooxy(phenyl)borinic acid Chemical compound ClOB(O)C1=CC=CC=C1 ZOQCZTRFTARYGJ-UHFFFAOYSA-N 0.000 description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JPWKWIRNTXBCSQ-UHFFFAOYSA-N C(C)(=O)O.C1(=CC=CC=C1)PC1=CC=CC=C1 Chemical compound C(C)(=O)O.C1(=CC=CC=C1)PC1=CC=CC=C1 JPWKWIRNTXBCSQ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IQJJOTYFOQNFTE-UHFFFAOYSA-N [B].C1(=CC=CC=C1)Cl Chemical compound [B].C1(=CC=CC=C1)Cl IQJJOTYFOQNFTE-UHFFFAOYSA-N 0.000 description 1
- GLFAEFVIKYUOJK-UHFFFAOYSA-N [B].[Cl] Chemical compound [B].[Cl] GLFAEFVIKYUOJK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
-
- 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
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- 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
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
-
- 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
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种钯配合物的制备方法,该方法将醋酸钯溶液和三苯基膦溶液混合后超声反应1.5h~5h,过滤,得到黄色结晶钯配合物。本发明以醋酸钯为原料,合成原料易得,成本低,在超声条件下进行反应,制备的产品以晶体形式析出,纯度高,产率高,操作过程简单,利于放大生产;采用本发明的方法制备的钯配合物在交叉偶合反应、铃木偶联反应中呈现优良的催化作用。采用本发明的方法制备的钯配合物的质量纯度≥99%,收率可达98%以上。
Description
技术领域
本发明属于金属配合物制备技术领域,具体涉及一种钯配合物的制备方法。
背景技术
在所有的过渡金属中,钯在有机合成中的应用可谓最广泛,有机钯配合物可接受许多不同种类的官能团,可以促进各种生成C-C键和其它键的反应,而这些反应往往具有较高的化学选择性和区域选择性。三苯基膦醋酸钯在交叉偶合反应、铃木偶联反应中催化性能优异,在医药工业和有机工业中有着广泛的应用。
现有技术公开了一种二苯基膦醋酸钯的制备方法(Braunstein.P等),它是以二(苯甲腈)氯化钯为原料,与二苯基膦乙酸钠在二氯甲烷中反应得到土黄色的二苯基膦醋酸钯,需要使用苯甲腈高毒试剂,过程复杂,且收率只有43%。专利200410020835.X,权利说明书中涉及二苯基膦乙酸钯的合成,以氯亚钯酸钠为原料,与二苯基膦乙酸钠在室温下反应得到二苯基膦乙酸钯,收率93%。还未见三苯基膦醋酸钯的制备报道。
发明内容
本发明所要解决的技术问题在于针对上述现有技术的不足,提供一种钯配合物的制备方法。该方法以醋酸钯为原料,合成原料易得,成本低,在超声条件下进行反应,制备的产品以晶体形式析出,纯度高,产率高,操作过程简单,利于放大生产,制备的钯配合物在交叉偶合反应、铃木偶联反应中呈现优良的催化作用。
为解决上述技术问题,本发明采用的技术方案是:一种钯配合物的制备方法,其特征在于,包括:将醋酸钯溶液和三苯基膦溶液混合后超声反应1.5h~5h,过滤,得到黄色结晶钯配合物。
上述的一种钯配合物的制备方法,其特征在于,醋酸钯和三苯基膦的摩尔比为1:(2~2.2)。
上述的一种钯配合物的制备方法,其特征在于,所述醋酸钯溶液和三苯基膦溶液的体积比为1:(1.5~5)。
上述的一种钯配合物的制备方法,其特征在于,所述醋酸钯溶液的溶剂为冰醋酸、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺;所述三苯基膦溶液的溶剂为无水乙醇、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺。
上述的一种钯配合物的制备方法,其特征在于,所述超声反应的温度为60℃~80℃。
本发明与现有技术相比具有以下优点:
1、本发明以醋酸钯为原料,合成原料易得,成本低,在超声条件下进行反应,制备的产品以晶体形式析出,纯度高,产率高,操作过程简单,利于放大生产;采用本发明的方法制备的钯配合物在交叉偶合反应、铃木偶联反应中呈现优良的催化作用。
2、采用本发明的方法制备的钯配合物的质量纯度≥99%,收率可达98%以上。
下面结合附图和实施例,对本发明的技术方案做进一步的详细描述。
附图说明
图1为本发明实施例1制备的钯配合物的红外光谱图。
具体实施方式
本发明制备的钯配合物的结构式为:Pd(PPh3)2(AC)2,其中,Pd为二价钯离子,PPh3为三苯基膦,AC为醋酸根。
具体制备方法为:将醋酸钯溶液和三苯基膦溶液按照1:(1.5~5)的体积比混合后超声反应1.5h~5h,过滤,得到黄色结晶钯配合物;醋酸钯和三苯基膦的摩尔比为1:(2~2.2);所述醋酸钯溶液的溶剂为冰醋酸、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺;所述三苯基膦溶液的溶剂为无水乙醇、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺;超声反应的温度为60℃~80℃。
实施例1
将0.2g Pd(AC)2溶解于10mL冰醋酸(也可采用甲苯、二氯甲烷、二甲基亚砜或N-N-二甲基甲酰胺)中得醋酸钯溶液,将0.5g PPh3溶解于30mL无水乙醇(也可采用二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺)中得三苯基膦溶液,将醋酸钯溶液加入三苯基膦溶液中,超声60℃反应5h后冷却,过滤,得到黄色结晶钯配合物,收率为98.5%,产物质量纯度为99.5%。
对本实施例制备的钯配合物进行元素分析:计算值,C64.08,H4.80,P8.28,Pd14.20;实验值,C64.01,H4.79,P8.23,Pd14.15,其红外光谱见图1,从图中可以看出,1648cm-1和1430cm-1出现两个强的吸收峰,前者归属于反对称COO-伸缩振动,后者归属于对称COO-的伸缩振动。3054cm-1、1433cm-1、1080cm-1、746cm-1、689cm-1、525cm-1出现的吸收峰归属于配位Ph3P的吸收谱带。说明COO-、Ph3P和钯配位,生成了钯配合物Pd(PPh3)2(AC)2。
实施例2
将0.2g Pd(AC)2溶解于10mL二氯甲烷(也可采用甲苯、冰醋酸、二甲基亚砜或N-N-二甲基甲酰胺)中得醋酸钯溶液,将0.47g PPh3溶解于15mL N-N-二甲基甲酰胺(也可采用二氯甲烷、甲苯、二甲基亚砜或无水乙醇)中得三苯基膦溶液,将三苯基膦溶液加入醋酸钯溶液中,超声70℃反应3h后冷却,过滤,得到黄色结晶钯配合物,收率为98.2%,产物质量纯度为99%。
对本实施例制备的钯配合物进行元素分析:计算值,C64.08,H4.80,P8.28,Pd14.20;实验值,C64.06,H4.77,P8.26,Pd14.19。红外光谱图与图1相似,1650cm-1和1435cm-1出现两个强的吸收峰,前者归属于反对称COO-伸缩振动,后者归属于对称COO-的伸缩振动。3055cm-1、1430cm-1、1082cm-1、743cm-1、690cm-1、521cm-1出现的吸收峰归属于配位Ph3P的吸收谱带。说明COO-、Ph3P和钯配位,生成了钯配合物Pd(PPh3)2(AC)2。
实施例3
将0.2g Pd(AC)2溶解于10mL冰醋酸(也可采用甲苯、二氯甲烷、二甲基亚砜或N-N-二甲基甲酰胺)中得醋酸钯溶液,将0.51g PPh3溶解于50mL二氯甲烷(也可采用无水乙醇、甲苯、二甲基亚砜或N-N-二甲基甲酰胺)中得三苯基膦溶液,将三苯基膦溶液加入醋酸钯溶液中,超声80℃反应1.5h后冷却,过滤,得到黄色结晶钯配合物,收率为98%,产物质量纯度为99.3%。
对本实施例制备的钯配合物进行元素分析:计算值,C64.08,H4.80,P8.28,Pd14.20;实验值,C64.08,H4.82,P8.25,Pd14.21。红外光谱图与图1相似,1649cm-1和1433cm-1出现两个强的吸收峰,前者归属于反对称COO-伸缩振动,后者归属于对称COO-的伸缩振动。3056cm-1、1436cm-1、1085cm-1、740cm-1、688cm-1、523cm-1出现的吸收峰归属于配位Ph3P的吸收谱带。说明COO-、Ph3P和钯配位,生成了钯配合物Pd(PPh3)2(AC)2。
将本发明制备的钯配合物作为催化剂用于硼氯偶联反应,过程如下:向三口烧瓶中加入1mmol邻氯硝基苯,1.2mmol对氯苯硼酸,1.8mmol碳酸钾,催化剂(钯含量为0.005mmol),3mL乙醇,7mL水,连接冷凝管。通入氮气除去瓶中的空气,然后升温至所需温度搅拌回流,反应结束后取样进行HPLC分析,结果见下表:
表1邻氯硝基苯与对氯苯硼酸的偶联反应产物色谱分析结果
从表1中可以看出,实施例1、2和3制备得到的钯配合物在邻氯硝基苯和对氯苯硼酸的偶联反应中有良好的催化性能,远远超出对比催化剂的性能,这可能是由于本发明制备的钯配合物兼具醋酸根和三苯基膦基团,更有利于促进偶联反应。
以上所述,仅是本发明的较佳实施例,并非对本发明做任何限制,凡是根据发明技术实质对以上实施例所作的任何简单修改、变更以及等效结构变化,均仍属于本发明技术方案的保护范围内。
Claims (5)
1.一种钯配合物的制备方法,其特征在于,包括:将醋酸钯溶液和三苯基膦溶液混合后超声反应1.5h~5h,过滤,得到黄色结晶钯配合物。
2.根据权利要求1所述的一种钯配合物的制备方法,其特征在于,醋酸钯和三苯基膦的摩尔比为1:(2~2.2)。
3.根据权利要求1所述的一种钯配合物的制备方法,其特征在于,所述醋酸钯溶液和三苯基膦溶液的体积比为1:(1.5~5)。
4.根据权利要求1或3所述的一种钯配合物的制备方法,其特征在于,所述醋酸钯溶液的溶剂为冰醋酸、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺;所述三苯基膦溶液的溶剂为无水乙醇、二氯甲烷、甲苯、二甲基亚砜或N-N-二甲基甲酰胺。
5.根据权利要求1所述的一种钯配合物的制备方法,其特征在于,所述超声反应的温度为60℃~80℃。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910375471.3A CN110041374A (zh) | 2019-05-07 | 2019-05-07 | 一种钯配合物的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910375471.3A CN110041374A (zh) | 2019-05-07 | 2019-05-07 | 一种钯配合物的制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110041374A true CN110041374A (zh) | 2019-07-23 |
Family
ID=67281049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910375471.3A Pending CN110041374A (zh) | 2019-05-07 | 2019-05-07 | 一种钯配合物的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110041374A (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114456210A (zh) * | 2021-12-15 | 2022-05-10 | 浙江微通催化新材料有限公司 | 一种四(三苯基膦)钯(0)催化剂的合成方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101144012A (zh) * | 2007-10-26 | 2008-03-19 | 山西大学 | 含有空穴传输基团的蒽电致发光材料及其制备方法 |
CN101550164A (zh) * | 2009-05-08 | 2009-10-07 | 西安凯立化工有限公司 | 一种二氯双三苯基膦配合钯的制备方法 |
-
2019
- 2019-05-07 CN CN201910375471.3A patent/CN110041374A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101144012A (zh) * | 2007-10-26 | 2008-03-19 | 山西大学 | 含有空穴传输基团的蒽电致发光材料及其制备方法 |
CN101550164A (zh) * | 2009-05-08 | 2009-10-07 | 西安凯立化工有限公司 | 一种二氯双三苯基膦配合钯的制备方法 |
Non-Patent Citations (1)
Title |
---|
A. SEAYAD等: "Hydroesterification of styrene using an in situ formed Pd(OTs)2(PPh3)2 complex catalyst", 《JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114456210A (zh) * | 2021-12-15 | 2022-05-10 | 浙江微通催化新材料有限公司 | 一种四(三苯基膦)钯(0)催化剂的合成方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN112142570B (zh) | 一种对羟基联苯二酚的制备方法 | |
CN104084230A (zh) | 一种用于Knoevenagel反应固体催化剂的制备方法 | |
CN113717081A (zh) | 4,4′-二氯二苯砜的制备方法 | |
CN106892790B (zh) | 一种利用微通道反应装置制备氘代苯胺类化合物的方法 | |
CN110041374A (zh) | 一种钯配合物的制备方法 | |
CN110668967A (zh) | 一种α-酮酰胺化合物的光催化制备方法 | |
CN110606829B (zh) | 一种钯催化合成4-取代喹啉衍生物的方法 | |
CN108047187A (zh) | 一种氧杂蒽酮的制备方法 | |
CN103435477B (zh) | 一种合成对乙氧基苯甲酸的方法 | |
CN105669413B (zh) | 一种微波辐射制备2-甲基-1,4-萘醌的方法 | |
CN108276261A (zh) | 一种水相中催化分子氧氧化制备2-溴芴酮的方法 | |
CN103992278A (zh) | 一种胞嘧啶的合成方法 | |
CN105348285B (zh) | 一种低成本高收率制备腺嘌呤的方法 | |
CN103896945A (zh) | 一种简便的叶酸环保生产方法 | |
CN104311469B (zh) | 一种取代吲哚-3-乙酸的合成方法 | |
CN114605393A (zh) | 一种微通道连续流制备氯沙坦的方法 | |
CN105801565B (zh) | N-[3-氯-4-[(3-氟苯基)甲氧基]苯基]-6-[(5-甲酰基)呋喃-2-基]-4-喹唑啉胺制备方法 | |
CN101475447B (zh) | 2,4,6-三甲基苯酚的合成方法 | |
CN110963927A (zh) | 一种n-苄基苯胺类化合物的烯丙基化方法 | |
CN104230690B (zh) | 一种固体催化高效制备9-芴酮的方法 | |
CN104030906A (zh) | 一种液相氧化法制备9-芴酮的方法 | |
CN107245052A (zh) | 一种阿扎那韦制备方法 | |
CN105111060B (zh) | 一种由烯烃合成酮的方法 | |
CN106946920A (zh) | 一种4‑氨基苯硼酸衍生物的制备方法 | |
CN108707146A (zh) | 一种硝呋太尔的合成方法 |
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 | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190723 |