CN107827913A - 含1,10‑菲啰啉状的n‑杂环卡宾铜（i）配合物及用途 - Google Patents
含1,10‑菲啰啉状的n‑杂环卡宾铜（i）配合物及用途 Download PDFInfo
- Publication number
- CN107827913A CN107827913A CN201711179428.7A CN201711179428A CN107827913A CN 107827913 A CN107827913 A CN 107827913A CN 201711179428 A CN201711179428 A CN 201711179428A CN 107827913 A CN107827913 A CN 107827913A
- Authority
- CN
- China
- Prior art keywords
- ferrosin
- complex
- heterocycle carbine
- shapes
- imidazoles
- 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.)
- Granted
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 31
- 239000010949 copper Substances 0.000 title claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 18
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 17
- 238000005859 coupling reaction Methods 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 claims 1
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical class ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 claims 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims 1
- -1 6-chlorophenyl nitrile Chemical class 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 4
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000005054 naphthyridines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明公开了1,10‑菲啰啉状的N‑杂环卡宾铜（I）配合物（以及配合物单晶）及用途。本发明所述的1,10‑菲啰啉状的N‑杂环卡宾铜（I）配合物是以1,10‑菲啰啉状的N‑杂环卡宾为配体。本发明所述含1,10‑菲啰啉状的N‑杂环卡宾铜（I）配合物（以及配合物单晶）具有较高的稳定性，它还能作为催化剂很好的催化氯代芳烃和咪唑的偶联反应。
Description
本发明得到天津市自然科学基金（16JCYBJC19700）的资助。
技术领域
本发明涉及一种新型金属有机配位化合物及其用途，特别涉及金属铜有机配合物及用途，确切地说是一种新型的含1,10-菲啰啉状的N-杂环卡宾铜（I）配合物及用途。
背景技术
在现在的社会生产实践中，配合物的存在已经极为普遍，配合物的应用也逐渐增多，例如在化学反应中需要的催化剂等。 N-杂环卡宾具有给电子能力强、制备简便、易于修饰等等优点,近些年来引起了人们很大的研究兴趣。N-杂环卡宾过渡金属化合物已经被广泛应用于烯烃复分解、偶联反应、氢化反应等等的有机反应。
发明内容
新型的含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物并将它应用于催化领域。
本发明是通过以下技术方案实现的：
含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物具有如下结构式：
本发明进一步公开了含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的单晶数据如下：
本发明更进一步公开了含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的合成方法：
主要包括反应、分离和纯化，含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的合成方法包括反应、分离和纯化，其特征是以萘啶基团修饰的咪唑氯代盐为原料与氯化亚铜在碱性条件下反应，得到所述含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物。将所得含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物溶于二氯甲烷/石油醚混合溶剂中慢慢挥发得到相应的单晶。
本发明更进一步公开了含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及的配合物单晶）在氯代芳烃和咪唑的偶联反应中有较好的催化性能。实验结果显示，当选用碳酸钾作为碱，DMF作为溶剂，以含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物作为催化剂，催化氯代芳烃和咪唑的偶联反应，其中氯代芳烃，咪唑和碳酸钾的投料比为：1:1.2:2，在120℃条件下，反应1-12小时，仅用0.01当量催化剂，反应产率就能达到95%以上。
本发明公开的含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的特点在于：
(a)含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物结构新颖，目前未见和其结构完全相同的报道。
(b) 本发明所制备的含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及配合物单晶）可很好的应用于催化氯代芳烃和咪唑的偶联反应，并显示出较好的催化性能。目前还未发现任何一种N-杂环卡宾铜（I）配合物能催化该反应。
附图说明
图1：含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的晶体结构图。
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。
实验中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。本发明所使用的核磁共振仪器的型号为BrukerAvance III 400 M小时z，单晶衍射仪型号为APEX II CCD。
实施例1
含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的合成路线和步骤如下：
取以萘啶基团修饰的咪唑氯代盐（50 mg, 0.14 mmol），氯化亚铜(13.6 mg, 0.14mmol)和碳酸钾(38 mg, 0.38 mmol)发生反应，保持温度为60 ℃，用丙酮回流24小时后，沉淀用二氯甲烷洗涤，过滤干燥，得到最终晶体530 mg (产率:75%)。
产物核磁共振数据：1H-NMR (400 MHz, CDCl3) δ (ppm): 1.12 (d, 12H), 2.27(m, 2H), 7.21 (d, 3H), 7.30 (d,1 H), 7.39-7.46 (m, 3H), 8.0 (d,1 H), 8.66 (s,1 H)。
实施例2
含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及配合物单晶）催化氯代芳烃和咪唑的偶联反应的应用：
在120度条件下，选用碳酸钾作为碱，DMF作为溶剂，以含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物作为催化剂，催化氯代芳烃和咪唑的偶联反应 ，其中氯代芳烃，咪唑和碳酸钾的投料比为：1:1.2:2。反应结束后，反应液用水洗，以二氯甲烷萃取三次，有机层合并，加无水硫酸镁干燥，浓缩，产物用柱色谱法提纯，得到相应产率。反应结果如下表1所示:
表1：含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及配合物单晶）在氯代芳烃和咪唑的偶联反应中的应用
结论：从表中可以看出，当选用碳酸钾作为碱，DMF作为溶剂，以含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及配合物单晶）作为催化剂，催化氯代芳烃和咪唑的偶联反应，其中氯代芳烃，咪唑和碳酸钾的投料比为：1:1.2:2，在120度条件下，用0.01当量催化剂，反应1-12小时，反应产率就能达到95%以上。目前还未发现任何一种N-杂环卡宾铜（I）配合物能催化该类反应。
本发明的方法，考察了现有的金属铜配合物催化氯代芳烃和咪唑的偶联反应，并进行了比较，在相同的反应条件下结果如下：
比较试验
结论：只有本发明专利报道的含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物（以及配合物单晶）作为催化剂，在上述反应条件下，反应产率才能达到95%以上，其他催化剂产率都低于90%。
Claims (5)
1.1,10-菲啰啉状的N-杂环卡宾铜（I）配合物具有如下结构式：
结构式。
2.含1,10-菲啰啉状的N-杂环卡宾铜（I）配合物的单晶，其特征在于该单晶结构采用APEX II CCD单晶衍射仪，使用经过石墨单色化的Mok α射线，λ = 0.71073 Å为入射辐射，以w-2q扫描方式收集衍射点，经过最小二乘法修正得到晶胞参数，从差值Fourier电子密度图利用软件解得单晶数据：
。
3.权利要求1所述含1,10-菲啰啉状的N-杂环卡宾铜（I）配合物作为催化剂在氯代芳烃和咪唑的偶联反应中的应用。
4.权利要求2所述含1,10-菲啰啉状的N-杂环卡宾铜（I）配合物单晶在用于催化氯代芳烃和咪唑的偶联反应方面的应用。
5.一种采用权利要求2所述的1,10-菲啰啉状的N-杂环卡宾铜（I）配合物单晶作为催化剂，催化氯代芳烃和咪唑进行偶联反应的方法，其特征在于：氯代芳烃和咪唑的偶联反应在120 ℃条件下，选用碳酸钾作为碱，DMF作为溶剂，以含有1,10-菲啰啉状的N-杂环卡宾铜（I）配合物单晶作为催化剂，催化氯代芳烃和咪唑的偶联反应，反应结束后，经后处理得到相应产物；其中氯代芳烃，咪唑和碳酸钾的投料比为：1:1.2:2，所述的催化剂的用量为0.01当量；所述的氯代芳烃指的是对硝基氯苯，2,4-二硝基氯苯，对氯苯腈，2,6-二氯吡啶。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711179428.7A CN107827913B (zh) | 2017-11-23 | 2017-11-23 | 含1,10-菲啰啉状的n-杂环卡宾铜（i）配合物及用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711179428.7A CN107827913B (zh) | 2017-11-23 | 2017-11-23 | 含1,10-菲啰啉状的n-杂环卡宾铜（i）配合物及用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107827913A true CN107827913A (zh) | 2018-03-23 |
| CN107827913B CN107827913B (zh) | 2020-01-10 |
Family
ID=61652417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711179428.7A Expired - Fee Related CN107827913B (zh) | 2017-11-23 | 2017-11-23 | 含1,10-菲啰啉状的n-杂环卡宾铜（i）配合物及用途 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107827913B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320626A (zh) * | 2018-12-17 | 2020-06-23 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光材料、其制备方法及有机电致发光器件 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1518534A (zh) * | 2001-04-24 | 2004-08-04 | 麻省理工学院 | 铜-催化的碳-杂原子键和碳-碳键的形成 |
| CN102558024A (zh) * | 2012-01-16 | 2012-07-11 | 山东盛华电子新材料有限公司 | 一种催化体系催化芳胺n-烷基化的方法 |
| CN104910195A (zh) * | 2015-04-21 | 2015-09-16 | 福州大学 | 一种二氟卡宾铜试剂及其制备和应用 |
| CN105944762A (zh) * | 2016-05-09 | 2016-09-21 | 武汉工程大学 | 菲啰啉类铜配合物催化剂及其制备方法和应用 |
| CN106478687A (zh) * | 2016-09-26 | 2017-03-08 | 广西师范大学 | 以1‑(2‑吡啶)‑9‑乙基‑β‑咔啉为配体的氯化铜配合物及其合成方法和应用 |
-
2017
- 2017-11-23 CN CN201711179428.7A patent/CN107827913B/zh not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1518534A (zh) * | 2001-04-24 | 2004-08-04 | 麻省理工学院 | 铜-催化的碳-杂原子键和碳-碳键的形成 |
| CN102558024A (zh) * | 2012-01-16 | 2012-07-11 | 山东盛华电子新材料有限公司 | 一种催化体系催化芳胺n-烷基化的方法 |
| CN104910195A (zh) * | 2015-04-21 | 2015-09-16 | 福州大学 | 一种二氟卡宾铜试剂及其制备和应用 |
| CN105944762A (zh) * | 2016-05-09 | 2016-09-21 | 武汉工程大学 | 菲啰啉类铜配合物催化剂及其制备方法和应用 |
| CN106478687A (zh) * | 2016-09-26 | 2017-03-08 | 广西师范大学 | 以1‑(2‑吡啶)‑9‑乙基‑β‑咔啉为配体的氯化铜配合物及其合成方法和应用 |
Non-Patent Citations (2)
| Title |
|---|
| MARGIT KRIECHBAUM ET AL.: "Silver and Gold Complexes with a New 1,10-Phenanthroline Analogue NHeterocyclic Carbene: A Combined Structural, Theoretical, and Photophysical Study", 《CHEM. EUR. J.》 * |
| 蔡良珍等: "串联的铜、钯催化偶联-环化合成二芳胺基芴", 《有机化学》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111320626A (zh) * | 2018-12-17 | 2020-06-23 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光材料、其制备方法及有机电致发光器件 |
| WO2020125239A1 (zh) * | 2018-12-17 | 2020-06-25 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光材料、其制备方法及有机电致发光器件 |
| JP2022513608A (ja) * | 2018-12-17 | 2022-02-09 | 広東阿格蕾雅光電材料有限公司 | 有機エレクトロルミネッセンス材料及びその調製方法並びに有機エレクトロルミネッセンスデバイス |
| CN111320626B (zh) * | 2018-12-17 | 2022-09-02 | 广东阿格蕾雅光电材料有限公司 | 有机电致发光材料、其制备方法及有机电致发光器件 |
| JP7130872B2 (ja) | 2018-12-17 | 2022-09-05 | 広東阿格蕾雅光電材料有限公司 | 有機エレクトロルミネッセンス材料及びその調製方法並びに有機エレクトロルミネッセンスデバイス |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107827913B (zh) | 2020-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107880079B (zh) | 环状氮杂环双卡宾钯配合物及其制备方法与用途 | |
| CN109438717B (zh) | 一种金属有机框架材料及其制备方法和应用 | |
| Xu et al. | Two 2D→ 3D entangled coordination polymers with polycatenated and polythreaded features based on 4 4-sql layers | |
| CN107176901A (zh) | 一种二氟亚甲基化合物的合成方法 | |
| CN107827913A (zh) | 含1,10‑菲啰啉状的n‑杂环卡宾铜（i）配合物及用途 | |
| CN103193808A (zh) | 一种手性锌配合物 | |
| Fan et al. | Salen-type nickel (II), palladium (II) and copper (II) complexes having chiral and racemic camphoric diamine components | |
| CN105504305B (zh) | 一种含3‑（4‑吡啶）吡唑‑丙酸的配位聚合物及其制备方法、用途 | |
| CN110283333B (zh) | 一种三维层柱结构双配体锌配合物及其制备方法 | |
| Gu et al. | A pair of novel Zn (II) enantiomeric coordination polymers based on a chiral multicarboxylate ligand: synthesis, crystal structures and molecular recognition properties | |
| CN115806504B (zh) | 一种不对称手性配体及其制备方法、制备的催化剂、合成方法及应用 | |
| CN109516986A (zh) | 2,4,4,8,8-五硝基-2-氮杂金刚烷及其合成方法 | |
| KR20150085676A (ko) | 지르코늄을 함유한 금속유기골격체를 촉매로 사용한 글리세롤카보네이트의 제조방법 | |
| CN106349163B (zh) | 一种基于Cu(I)的金属有机配位聚合物及其制备方法与应用 | |
| CN105601472B (zh) | 新型5‑[4‑(1‑羧基萘基)]‑间苯二甲酸的制备方法 | |
| CN104130292A (zh) | 一种带双核结构的三维配位聚合物及其制备方法 | |
| Tang et al. | Coinage Metal (Bisfluorosulfonyl) imide Complexes: Preparation, Characterization, and Catalytic Applications | |
| CN104402813B (zh) | 一种索拉非尼的制备方法 | |
| CN110330515B (zh) | 一种氮氧混合配体锌配合物及其制备方法 | |
| CN105924390A (zh) | 一种美他非尼的合成方法 | |
| Yuan et al. | In situ selective ligand transformation from Si–H to Si–OH for synergistic assembly of hydrogen-bonded metal–organic frameworks | |
| CN106694038B (zh) | 四甲基铵二锌-钒氧簇催化剂、制备方法及其用途 | |
| CN104557986B (zh) | 具有催化对氟苯硼酸的三唑-三氟甲基磺酸铜配合物及其制备方法 | |
| CN103910668B (zh) | 一种3‑烷基吲哚的制备方法 | |
| CN105732671A (zh) | 一种含螺旋的镉金属有机框架荧光材料及其制备方法 |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200110 Termination date: 20211123 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |