CN106243151A - 一种钯配合物的改进合成方法 - Google Patents
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 31
- 238000010189 synthetic method Methods 0.000 title claims abstract description 17
- 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 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 21
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 13
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 12
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims abstract description 8
- -1 reaction Substances 0.000 claims abstract description 8
- 235000009518 sodium iodide Nutrition 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000000605 extraction Methods 0.000 claims abstract description 3
- 229910021606 Palladium(II) iodide Inorganic materials 0.000 claims description 13
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 229910021605 Palladium(II) bromide Inorganic materials 0.000 claims description 10
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
- 150000001502 aryl halides Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000007341 Heck reaction Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
- UDHAWRUAECEBHC-UHFFFAOYSA-N 1-iodo-4-methylbenzene Chemical compound CC1=CC=C(I)C=C1 UDHAWRUAECEBHC-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical group BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical group ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic 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
- 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
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2247—At least one oxygen and one phosphorous atom present as complexing atoms in an at least bidentate or bridging ligand
-
- 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
- B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开一种钯配合物(通式中X=Br 或 I)的改进合成方法,属于有机化学领域。其特征在于以PdCl2(PPh3)2与碘化钠或溴化钠为原料,其投料摩尔比为1:10。二氯甲烷和水按体积比1:1作为溶剂,反应制得,产品经萃取、洗涤、过滤处理后,得到高质量的PdX2(PPh3)2钯配合物。本发明的钯配合物收率高,方法更简单,原料更廉价,具有良好的工业化应用前景。
Description
本发明的到天津市自然科学基金(No.16JCYBJC19700)资助。
技术领域
本发明涉及一种钯配合物的改进合成方法,属于有机化学领域。
背景技术
PdX2(PPh3)2(X=I或Br)钯配合物作为一种高效的催化Heck偶联反应的催化剂在我们以前专利201610352690.6中已进行了详细报道。
对于此类配合物的合成方法目前报道也并不是很多,对于配合物PdBr2(PPh3)2,已有文献报道的合成方法主要有以下几种:1)以四三苯基磷钯和1,2-二溴乙烯为原料,THF为溶剂(Gazzetta Chimica Italiana, 1988, 118, 469);2)以PdCl2(CH3CN)2和溴化锂为原料(Chemistry-Aeurpoean Journal, 2012, 18, 12803);3)以PdCl2(PPh3)2和4-二甲基氨基吡啶氢溴酸盐作原料,在加热条件下制备(Acta Crystallographica Section E,2009,E65, m940)。这三种方法所用原料都相对比较昂贵,同时反应条件也较为复杂苛刻。
对于配合物PdI2(PPh3)2已有文献报道的合成方法主要以碘化钯和三苯基膦为原料(Zeitschrift fuer Naturforschung, B: Chemical Science, 2004, 59, 196),该方法虽然操作简单,条件温和,但碘化钯却十分昂贵,工业化困难。
我们在专利201610352690.6中对其合成方法也进行了初步改进。PdBr2(PPh3)2的合成方法是以邻氯吡啶为初始原料,先与碘甲烷反应,再与四(三苯基膦)钯反应制得。所述的钯配合物PdI2(PPh3)2的合成方法是以邻溴吡啶为初始原料,先与碘乙酸反应,再与四(三苯基膦)钯反应制得。这两种方法易操作、易控制,所得产物纯度和收率较高。
随着试验的不断深入,本发明人发现201610352690.6公开的制备方法中存在合成步骤较多,提纯较复杂的缺陷。为了更好地适应工业生产的需要,发明一种原料更加廉价、步骤更加简单,条件更加温和,产率相对较高的方法仍然很有必要。
发明内容
本发明的一个目的在于提供一种钯配合物的改进合成方法。
本发明提供的钯配合物的改进合成方法简单、快捷、原料廉价易得、产率高,与已报道的文献、专利具有明显的不同。
本发明是通过以下技术方案实现的:
一种钯配合物的改进合成方法,其特征在于以PdCl2(PPh3)2与碘化钠或溴化钠为原料,二氯甲烷和水按体积比1:1作为溶剂,反应制得,产品经萃取、洗涤、过滤处理后,得到高质量的PdX2(PPh3)2钯配合物,其钯配合物的结构如下:
本发明以PdCl2(PPh3)2与碘化钠或溴化钠为原料,投料摩尔比为1:10。反应温度为室温。
本发明进一步公开了钯配合物改进合成方法制备的PdX2(PPh3)2钯配合物在用于Heck偶联反应方面的应用。其中所述用于Heck偶联反应指的是:含有钯配合物的催化剂PdI2(PPh3)2或PdBr2(PPh3)2对芳基卤代烃和丙烯酸乙酯的Heck偶联反应。
本发明公开的方法与201610352690.6公开的制备方法的不同点在于:
(1)产物经一步反应获得,操作方法更简单、快捷、原料更廉价易得。
(2)产品提纯更简便,反应收率更高,可以达到90%。更适合大规模的工业化生产。
附图说明
图1:钯配合物的结构式。
具体实施方式
下面通过具体的实施方案叙述本发明。除非特别说明,本发明中所用的技术手段均为本领域技术人员所公知的方法。另外,实施方案应理解为说明性的,而非限制本发明的范围,本发明的实质和范围仅由权利要求书所限定。对于本领域技术人员而言,在不背离本发明实质和范围的前提下,对这些实施方案中的物料成分和用量进行的各种改变或改动也属于本发明的保护范围。
所有的原料都是从国内的化学试剂公司进行购买,没有经过继续提纯而直接使用。
实施例1
PdI2(PPh3)2钯配合物的合成步骤如下:
将PdCl2(PPh3)2 (50 mg, 0.071 mmol),NaI (107 mg, 0.71 mmol),10 mL二氯甲烷,以及10 mL水依次加入到50 mL的圆底烧瓶中,反应室温搅拌8小时后将有机层分离,用无水硫酸钠干燥,过滤浓缩,粗产品经二氯甲烷/石油醚重结晶得到红色晶体即为PdI2(PPh3)2配合物,产率: 90%。产物核磁共振及元素分析数据:1H-NMR (400 MHz, CDCl3) δ (ppm):7.71-7.66 (m, 12H, CHar), 7.46-7.37 (m, 18H, CHar); 13C-NMR (100 MHz, CDCl3) δ(ppm): 135.0, 132.0, 131.2, 128.1。
实施例2
PdI2(PPh3)2钯配合物的合成步骤如下:
将PdCl2(PPh3)2 (50 mg, 0.071 mmol),NaBr (74 mg, 0.71 mmol),10 mL二氯甲烷,以及10 mL水依次加入到50 mL的圆底烧瓶中,反应室温搅拌8小时后将有机层分离,用无水硫酸钠干燥,过滤浓缩,粗产品经二氯甲烷/石油醚重结晶得到红色晶体即为PdBr2(PPh3)2配合物,产率: 85%。
产物核磁共振及元素分析数据:1H-NMR (400 MHz, CDCl3) δ (ppm): 7.72-7.67 (m,12H, CHar), 7.38-7.34 (m, 18H, CHar); 13C-NMR (100 MHz, CDCl3) δ (ppm): 135.2,134.0, 130.2, 127.6。
实施例3
催化剂PdBr2(PPh3)2 和PdI2(PPh3)2对Heck偶联反应催化活性测试方法及结果如下:
(a)反应瓶抽真空通氮气,依次加入设定量的催化剂PdI2(PPh3)2或PdBr2(PPh3)2,卤代芳烃(3 mmol),丙烯酸乙酯(360mg, 3.6 mmol), 三乙胺(455mg, 4.5 mmol),DMF (1 mL),恒温110oC搅拌反应12 h。反应结束后,冷却至室温,水洗,二氯甲烷萃取三次,有机层合并,干燥浓缩,过柱子提纯,收集产物带,浓缩称重,计算产率。反应结果如下:
催化剂PdI2(PPh3)2和PdI2(PPh3)2应用于卤代芳烃和丙烯酸乙酯的Heck偶联反应中的催化活性测试结果:
在已选定的最佳条件下,本实施例对高效钯催化剂PdI2(PPh3)2或PdBr2(PPh3)2应用于对不同卤代芳烃和丙烯酸乙酯的Heck反应中的催化活性进行了进一步的探究。通过以上探究我们发现,催化剂PdI2(PPh3)2催化4-溴碘苯和丙烯酸乙酯的Heck反应的TON值为2.0 x109 (entry 5,),同样的,催化剂PdBr2(PPh3)2催化4-甲基碘苯和丙烯酸乙酯的Heck反应的TON值为1.9 x 109 (entry 6)。与此同时,碘苯与丙烯酸乙酯的反应也得到了类似较高的TON值。由此可知,催化剂PdI2(PPh3)2或PdBr2(PPh3)2对各种碘代芳烃均具有较好的催化效果。当使用4-溴硝基苯做底物时,催化剂PdI2(PPh3)2和PdBr2(PPh3)2分别得到了4.0 x 105 (entry 9) 和 3.4 x 105 (entry 9)这样一组相对较低的TON值。在使用对溴苯甲醛和溴苯做底物时,也得到了相似的较低的TON值(entry 11-14)。由此可以看出,碘代芳烃活性要远远高于溴代芳烃。
Claims (5)
1.一种钯配合物的改进合成方法,其特征在于以PdCl2(PPh3)2与碘化钠或溴化钠为原料,二氯甲烷和水按体积比1:1作为溶剂,反应制得,产品经萃取、洗涤、过滤处理后,得到高质量的PdX2(PPh3)2钯配合物,其钯配合物的结构如下:
X = Br 或 I。
2.权利要求1 所述钯配合物的改进合成方法,其特征在于以PdCl2(PPh3)2与碘化钠或溴化钠为原料,投料摩尔比为1:10。
3.权利要求1 所述钯配合物的改进合成方法,其特征在于反应温度为室温。
4.采用权利要求1所述钯配合物改进合成方法制备的PdX2(PPh3)2钯配合物在用于Heck偶联反应方面的应用。
5.权利要求4所述的应用,其中所述用于Heck偶联反应指的是:含有钯配合物的催化剂PdI2(PPh3)2或PdBr2(PPh3)2对芳基卤代烃和丙烯酸乙酯的Heck偶联反应。
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CN110330528A (zh) * | 2019-07-08 | 2019-10-15 | 西安凯立新材料股份有限公司 | 一种双(三苯基膦)溴化钯的制备方法 |
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---|---|---|---|---|
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---|---|---|---|---|
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Non-Patent Citations (3)
Title |
---|
ANTHONY FULFORD ET AL: "Dibromobis(triphenylphosphine)-palladium(II)", 《E-EROS ENCYCLOPEDIA OF REAGENTS FOR ORGANIC SYNTHESIS》 * |
HMAHALAKSHMI ET AL.: "o-Diphenylphosphinobenzaldehyde complexes of palladium(II) and platinum(II):synthesis, spectroscopy and structure", 《INDIAN JOURNAL OF CHEMISTRY》 * |
高宏飞等: "新型含氮三齿钯(II)配合物的合成及其催化性能研究", 《有机化学》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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