CN107827913B - 含1,10-菲啰啉状的n-杂环卡宾铜（i）配合物及用途 - Google Patents
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- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 title claims abstract description 21
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims abstract description 18
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 12
- 238000005859 coupling reaction Methods 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 23
- 239000013078 crystal Substances 0.000 abstract description 13
- -1 N-heterocyclic carbene copper (I) complexes Chemical class 0.000 abstract description 10
- 150000002460 imidazoles Chemical class 0.000 abstract description 7
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 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
- 230000003197 catalytic effect Effects 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical class [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 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
- 238000005865 alkene metathesis reaction Methods 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
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- 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
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- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
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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 (1)
1.一种含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；所述的1,10-菲啰啉状的N-杂环卡宾铜（I）配合物具有如下结构式：
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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
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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 |
|---|
| Silver and Gold Complexes with a New 1,10-Phenanthroline Analogue NHeterocyclic Carbene: A Combined Structural, Theoretical, and Photophysical Study;Margit Kriechbaum et al.;《Chem. Eur. J.》;20121231;第18卷;page: 5506-5509 * |
| 串联的铜、钯催化偶联-环化合成二芳胺基芴;蔡良珍等;《有机化学》;20151231;第1682-1690页 * |
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