CN105949223A - 一种双核银三联吡啶配合物的制备方法 - Google Patents
一种双核银三联吡啶配合物的制备方法 Download PDFInfo
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- 229910052709 silver Inorganic materials 0.000 title claims abstract description 32
- 239000004332 silver Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 39
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 241001597008 Nomeidae Species 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000003760 magnetic stirring Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- ZOIOVSMWGBSJGP-UHFFFAOYSA-N silver silver nitrate Chemical compound [Ag].[Ag+].[O-][N+]([O-])=O ZOIOVSMWGBSJGP-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- 125000005469 ethylenyl group Chemical group 0.000 claims 1
- XRRQZKOZJFDXON-UHFFFAOYSA-N nitric acid;silver Chemical compound [Ag].O[N+]([O-])=O XRRQZKOZJFDXON-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000006053 organic reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C=C(*)C=C(C)C(N=*1)=C[C@@](*)CC1C1=NC=C[C@]2C1=C2*)N Chemical compound CC(C=C(*)C=C(C)C(N=*1)=C[C@@](*)CC1C1=NC=C[C@]2C1=C2*)N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000006713 insertion reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/10—Silver compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本方法提供了一种在温和条件下,硝酸银与三联吡啶化合物制备双核银三联吡啶配合物的方法。该反应的优点是操作简单,反应易于控制,且能够选择性的得到双配位的双核银配合物。本发明涉及的制备硝酸银三联吡啶的双核银配合物,化学反应方程式如下:包括将硝酸银和一种三联吡啶衍生物1在乙腈为溶剂的条件下,制备双核银配合物2。R可以为氢/叔丁基/甲基/甲氧基/乙基/苯基/异丙基/叔丁氧基等保护基团。
Description
技术领域
本发明属于有机合成化学技术领域,具体涉及一种双核银三联吡啶配合物的制备方法。
背景技术
近几十年,银催化的有机化学反应受到越来越多的关注[Chem. Soc. Rev.,2007, 36, 759–769; Chem. Rev., 2008, 108, 2793–2795; Silver in Organic Chemistry, ed. M. Harmata, Wiley, Hoboken,
NJ, 2010; Chem. Soc. Rev., 2015, 44, 8124-8173; Chem. Commun., 2016, 52,853-868.]。通过不断的文献报道发现,银作为催化剂在催化有机反应时表现出其独有的一些催化性质,为了更进一步拓展银催化的有机反应,近年来越来越多的银配合物被用于催化有机反应,并且表现出与简单银盐截然不同的催化性能。然而目前所合成的银配合物大多为单核银配合物。在2003年,芝加哥大学的He Chuan课题组在实验室通过简单银盐与三联吡啶合成了一种双核银的三联吡啶配合物(J. Am. Chem. Soc., 2003, 125 (52),16202–16203),并且在实验过程中发现这类配合物对乃春插入反应具有独特的催化活性,在实验过程中发现双核银配合物与单核银配合物在催化有机反应时具有截然不同的催化性能[Angewandte Chemie, International Edition, 2004, 43(32), 4210-4212;Org. Lett., 2005, 7 (22), 4983–4985;Eur. J. Org. Chem.,2006, 4313–4322;Angewandte Chemie International Edition, 2007, 46(27), 5184–5186.]。因此,如何发展一种新的双核银配合物对于进一步推动银催化剂在有机化学中的发展具有重要的意义。
本发明利用简单易得的硝酸银与三联吡啶化合物在常温条件下制备了一系列全新的双核银三联吡啶配合物,该类双核银配合物的制备此前从未有人报道过。
发明内容
本方法提供了一种在温和条件下,硝酸银与三联吡啶化合物制备双核银三联吡啶配合物的方法。该反应的优点是操作简单,反应易于控制,且能够选择性的得到双配位的双核银配合物。
本发明涉及的制备硝酸银三联吡啶的双核银配合物,化学反应方程式如下:
包括将硝酸银和一种三联吡啶衍生物1在乙腈为溶剂的条件下,制备双核银配合物2。R可以为氢/叔丁基/甲基/甲氧基/乙基/苯基/异丙基/叔丁氧基等保护基团,包括但不限于上述已经列出的。
步骤、条件:向带有磁力搅拌装置的容器中加入溶剂乙腈、二甲基亚砜、1,2-二氯乙烷、N,N-二甲基甲酰胺、1,4-二氧六环、二氯甲烷其中之一5 mL,硝酸银,4,4′,4″-三叔丁基-2,2′:6′,2″-三联吡啶、4,4′,4″-三甲基-2,2′:6′,2″-三联吡啶、4,4′,4″-三甲氧基-2,2′:6′,2″-三联吡啶、4,4′,4″-三乙基-2,2′:6′,2″-三联吡啶其中之一,将其放入20-60℃油浴中,继续搅拌。硝酸银与三联吡啶化合物的摩尔比为1:1-2.5,5-30分钟后,将反应容器中的混合物过滤,用乙腈洗涤滤饼3-5次,收集滤液并且在25℃减压蒸馏除去有机溶剂,得到白色固体,所得白色固体用乙腈重结晶,最后抽滤得到产物2。
附图说明
图1为2a的X-射线单晶衍射图;
图2为2a的XRD粉末衍射图;
图3为2a的全功能荧光光谱谱图;
图4为2a的紫外可见吸收光谱谱图;
图5为2a的1H-NMR核磁共振谱图;
图6为2a的13C-NMR核磁共振谱图。
具体实施方式
下面的实施例将有助于说明本发明,但是不局限其范围。
实施例1 三联吡啶双核银配合物2a的制备
向带有磁力搅拌装置的25mL圆底烧瓶中加入5.0 mL乙腈, 将4,4′,4″-三叔丁基-2,2′:6′,2″-三联吡啶1a (200 mg, 0.5mmol)溶解乙腈中,向反应溶液中加入硝酸银(85 mg,0.5 mmol),25℃条件下继续搅拌5min,将反应容器中的混合物过滤,用15mL乙腈洗涤滤饼3-5次,合并并收集滤液,在25℃减压蒸馏除去有机溶剂,得到白色固体,所得白色固体用乙腈重结晶,抽滤得到白色固体产物2a,其收率为86%。
谱图解析数据2a:
1H-NMR (500 MHz, CD3CN) δ 7.29 (t, J = 8.0 Hz, 2H), 7.94 (t, J = 7.0 Hz,1H), 6.90 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H);
13C-NMR (500 MHz, CD3CN) δ 159.5, 129.4, 120.6, 113.8, 55.1.
实施例2 三联吡啶双核银配合物2b的制备
用三联吡啶衍生物1b代替“实施例1”中的三联吡啶1a,其他步骤及用量均不变。实验结果见表1。
谱图解析数据2b:
1H-NMR (500 MHz, CD3CN) δ 7.29 (t, J = 8.0 Hz, 2H), 7.94 (t, J = 7.0 Hz,1H), 6.90 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H);
13C-NMR (500 MHz, CD3CN) δ 159.5, 129.4, 120.6, 113.8, 55.1.
实施例3 三联吡啶双核银配合物2c的制备
用三联吡啶衍生物1c代替“实施例1”中的三联吡啶1a,其他步骤及用量均不变。实验结果见表1。
谱图解析数据2c:
1H-NMR (500 MHz, CD3CN) δ 7.29 (t, J = 8.0 Hz, 2H), 7.94 (t, J = 7.0 Hz,1H), 6.90 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H);
13C-NMR (500 MHz, CD3CN) δ 159.5, 129.4, 120.6, 113.8, 55.1.
实施例4 三联吡啶双核银配合物2d的制备
用三联吡啶衍生物1d代替“实施例1”中的三联吡啶1a,其他步骤及用量均不变。实验结果见表1。
谱图解析数据2d:
1H-NMR (500 MHz, CD3CN) δ 7.29 (t, J = 8.0 Hz, 2H), 7.94 (t, J = 7.0 Hz,1H), 6.90 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H);
13C-NMR (500 MHz, CD3CN) δ 159.5, 129.4, 120.6, 113.8, 55.1.
实施例5 三联吡啶双核银配合物2e的制备
用三联吡啶衍生物1e代替“实施例1”中的三联吡啶1a,其他步骤及用量均不变。实验结果见表1。
谱图解析数据2e:
1H-NMR (500 MHz, CD3CN) δ 7.29 (t, J = 8.0 Hz, 2H), 7.94 (t, J = 7.0 Hz,1H), 6.90 (d, J = 8.5 Hz, 2H), 3.80 (s, 3H);
13C-NMR (500 MHz, CD3CN) δ 159.5, 129.4, 120.6, 113.8, 55.1.
表1
Claims (2)
1.一种双核银硝酸银三联吡啶配合物的制备方法,其特征是,化学反应方程式如下:
包括将硝酸银和一种三联吡啶衍生物1在乙腈为溶剂的条件下,制备双核银配合物2,R为氢/叔丁基/甲基/甲氧基/乙基/苯基/异丙基/叔丁氧基保护基团, 具体步骤、条件:向带有磁力搅拌装置的容器中加入溶剂乙腈、二甲基亚砜、1,2-二氯乙烷、N,N-二甲基甲酰胺、1,4-二氧六环、二氯甲烷其中之一5 mL,硝酸银,4,4′,4″-三叔丁基-2,2′:6′,2″-三联吡啶、4,4′,4″-三甲基-2,2′:6′,2″-三联吡啶、4,4′,4″-三甲氧基-2,2′:6′,2″-三联吡啶、4,4′,4″-三乙基-2,2′:6′,2″-三联吡啶其中之一,将其放入20-60℃油浴中,继续搅拌,硝酸银与三联吡啶化合物的摩尔比为1:1-2.5,5-30分钟后,将反应容器中的混合物过滤,用乙腈洗涤滤饼3-5次,收集滤液并且在25℃减压蒸馏除去有机溶剂,得到白色固体,所得白色固体用乙腈重结晶,最后抽滤得到产物2。
2.按权利要求1所述的双核银硝酸银三联吡啶配合物的制备方法,其特征是,化学反应方程式如下:
具体步骤、条件:向带有磁力搅拌装置的25mL圆底烧瓶中加入5.0 mL乙腈, 将4,4′,4″-三叔丁基-2,2′:6′,2″-三联吡啶1a,200 mg, 0.5mmol溶解乙腈中,向反应溶液中加入硝酸银85 mg, 0.5 mmol,25℃条件下继续搅拌5min,将反应容器中的混合物过滤,用15mL乙腈洗涤滤饼3-5次,合并并收集滤液,在25℃减压蒸馏除去有机溶剂,得到白色固体,所得白色固体用乙腈重结晶,抽滤得到白色固体产物2a,其收率为86%。
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