CN108610380B - 一种四吡啶基卟啉锌-钌配合物及其制备和应用 - Google Patents
一种四吡啶基卟啉锌-钌配合物及其制备和应用 Download PDFInfo
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- SBTXZBOBSRZUPE-UHFFFAOYSA-N 5,10,15,20-tetrapyridin-2-yl-21,23-dihydroporphyrin Chemical compound c1cc2nc1c(-c1ccccn1)c1ccc([nH]1)c(-c1ccccn1)c1ccc(n1)c(-c1ccccn1)c1ccc([nH]1)c2-c1ccccn1 SBTXZBOBSRZUPE-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 18
- AVAYXTKDRHARSR-UHFFFAOYSA-N [Zn].[Ru] Chemical compound [Zn].[Ru] AVAYXTKDRHARSR-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 17
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical class [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 16
- GPCVIABQWNSPHL-UHFFFAOYSA-N N1=C(C=CC=C1)C1=C2C=CC(C(=C3C=CC(=C(C=4C=CC(=C(C5=CC=C1N5)C5=NC=CC=C5)N4)C4=NC=CC=C4)N3)C3=NC=CC=C3)=N2.[Ru].[Zn] Chemical compound N1=C(C=CC=C1)C1=C2C=CC(C(=C3C=CC(=C(C=4C=CC(=C(C5=CC=C1N5)C5=NC=CC=C5)N4)C4=NC=CC=C4)N3)C3=NC=CC=C3)=N2.[Ru].[Zn] GPCVIABQWNSPHL-UHFFFAOYSA-N 0.000 claims abstract description 11
- NBMSMTXCRBADNF-UHFFFAOYSA-N 5,10,15,20-tetrapyridin-2-yl-21,23-dihydroporphyrin zinc Chemical compound [Zn].c1cc2nc1c(-c1ccccn1)c1ccc([nH]1)c(-c1ccccn1)c1ccc(n1)c(-c1ccccn1)c1ccc([nH]1)c2-c1ccccn1 NBMSMTXCRBADNF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052725 zinc Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- -1 ketone compound Chemical class 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 150000008365 aromatic ketones Chemical class 0.000 claims description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 abstract description 3
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 238000006276 transfer reaction Methods 0.000 abstract description 2
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 150000004032 porphyrins Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YIYFFLYGSHJWFF-UHFFFAOYSA-N [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 YIYFFLYGSHJWFF-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
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- KIQQAJNFBLKFPO-UHFFFAOYSA-N magnesium;porphyrin-22,23-diide Chemical compound [Mg+2].[N-]1C(C=C2[N-]C(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 KIQQAJNFBLKFPO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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- 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
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
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- 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
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- 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
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
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- 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
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
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- 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
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- Pyridine Compounds (AREA)
Abstract
本发明公开了一种四吡啶基卟啉锌‑钌配合物的合成及其应用。在室温条件下，以配位不饱和的钌金属配合物为原料与四吡啶基卟啉锌反应，合成具有较高催化活性的四吡啶基卟啉锌‑钌配合物。此四吡啶基卟啉锌‑钌配合物可应用于氢转移反应中，是制备二级醇的简便绿色的方法。
Description
技术领域
本发明涉及一种四吡啶基卟啉锌-钌配合物及其制备方法，以配位不饱和的单核钌金属配合物为原料，与四吡啶基卟啉锌在有机溶剂中发生配位反应，合成具有较高催化活性的四吡啶基卟啉锌-钌配合物。本发明具有操作简便、反应条件温和、合成效率高等优点。
技术背景
配位驱使的组装反应被广泛应用于合成不同类型的超分子化合物，如索烃、节状化合物等。这些超分子化合物在材料、光化学、电化学等方面存在潜在的应用前景。
近年来，利用卟啉作为前体合成各种类型的超分子化合物受到了广泛的关注，通过不同的组装与反应方式可以得到立体构型各异的卟啉超分子配合物，在多种催化领域有着较好的应用前景。2015年，Ema研究组(T.Ema,et al.Angew.Chem.Int.Ed.2015,54,134.)合成不同类型的卟啉锌及卟啉镁的超分子化合物，并成功应用于二氧化碳对环氧化合物的插入反应，高效的制备碳酸酯化合物，在材料及电化学方向有着潜在的应用价值。Anderson研究组(H.L.Anderson,et al.Angew.Chem.Int.Ed.2016,55,8358.)以五齿配体为模板剂成功合成了卟啉锌超分子环状化合物，具有较好的光化学性能。Kobayashi研究组(K.Kobayashiet,et al.J.Am.Chem.Soc.2016,138,12564.)利用卟啉铑配合物为前体，与具有多配位点的分子进行配位组装，通过调变官能团的不同，合成了不同类型的超分子卟啉铑配合物，并进行了单晶、核磁等一系列表征，在主客体化学中有广泛的应用前景。
本发明主要是利用四吡啶基卟啉锌与配位不饱和的金属钌作用，单核钌金属配合物中金属中心具有一个空位，可与四吡啶基卟啉锌配位性的原子进行配位，合成具有较高氢转移活性的四吡啶基卟啉锌-钌配合物，制备方法简单、产率高。此类四吡啶基卟啉锌-钌配合物性质稳定，对空气不敏感，易于保存。
发明内容
本发明的目的在于提供一种操作简便、反应条件温和、高收率的制备四吡啶基卟啉锌-钌配合物的方法。该四吡啶基卟啉锌-钌配合物性质稳定，对空气不敏感，易于保存。
为了实现上述目的，本发明的技术方案如下：
1一种四吡啶基卟啉锌-钌配合物，其结构式1如下：
利用配位不饱和的单核钌金属配合物2与四吡啶基卟啉锌3在有机溶剂中进行反应合成四吡啶基卟啉锌-钌配合物1；
四吡啶基卟啉锌3的结构式如下：
四吡啶基卟啉锌-钌配合物1的合成路线如下述反应式所示：
单核钌金属配合物2与四吡啶基卟啉锌3的反应溶剂为二氯甲烷、甲醇、乙醇和甲苯中的一种或者两种。
单核钌金属配合物2与四吡啶基卟啉锌3的摩尔比范围为1:1-10:1，单核钌金属配合物2与四吡啶基卟啉锌3的摩尔比优选为4:1。
单核钌金属配合物2与四吡啶基卟啉锌3的反应温度为20-110℃，优选为78℃；反应时间为1-24h。
反应气氛为氮气，压力条件为一个大气压。
将反应体系减压浓缩后用二氯甲烷/正己烷(v/v＝1/3)重结晶即可得到四吡啶基卟啉锌-钌配合物1。
所述酮类化合物为芳香酮，脂肪酮。
氮气氛围下异丙醇中回流，在较低催化剂浓度下，即可将酮类化合物转化为相应的醇类化合物。
本发明具有以下优点：
1)四吡啶基卟啉锌-钌配合物合成路线简单，条件温和，可方便快捷的合成出目标产物。
2)四吡啶基卟啉锌-钌配合物性质稳定，对空气不敏感，易于保存。
3)四吡啶基卟啉锌-钌配合物可用于高效催化酮的氢转移反应。
具体实施方式
本发明以单核钌金属配合物2为原料，与四吡啶基卟啉锌3按4:1摩尔比在有机溶剂中发生配位反应，合成四吡啶基卟啉锌-钌配合物1。通过下述实施例有助于进一步理解本发明，但本发明的内容并不仅限于此。
单核钌金属配合物2按文献方法制备(Yu,Z.K.et al.Organometallics2008,27,2898.)；四吡啶基卟啉锌3按文献方法制备(D.B.Amabilino,et al.J.Am.Chem.Soc.2015,137,15795.)
实施例1
氮气条件下，配位不饱和的单核钌金属配合物2(27mg,0.04mmol)、四吡啶基卟啉锌(6.8mg,0.01mmol)，在3mL的乙醇溶剂中78℃搅拌1h。减压下除去挥发组份，固体用CH2Cl2/正己烷(v:v＝1:3)重结晶，得到黄绿色固体为目标产物1(32mg，收率95％)。目标产物通过核磁共振谱与元素分析测定得到确认。
实施例2
反应步骤与操作同实施例1，与实施例1不同之处在于，体系反应时间为24h。停止反应后，经后处理得到黄绿色固体为目标产物1(30mg,收率89％)。说明延长反应时间对增加目标产物收率无益。
实施例3
反应步骤与操作同实施例1，与实施例1不同之处在于，反应溶剂为甲苯，反应温度为110℃。停止反应后，经后处理得到黄绿色固体为目标产物1(29mg,收率86％)。说明在非质子性溶剂中也能进行此反应。
实施例4
反应步骤与操作同实施例1，与实施例1不同之处在于，反应溶剂为二氯甲烷/甲醇(v/v,5/1)，反应温度为28℃。停止反应后，经后处理得到黄绿色固体为目标产物1(25mg,收率74％)。说明在混合溶剂中也能进行此反应。
实施例5
反应步骤与操作同实施例1，与实施例1不同之处在于，体系反应温度为50℃。停止反应后，经后处理得到黄绿色固体为目标产物1(27mg,收率80％)。
实施例6
反应步骤与操作同实施例1，与实施例1不同之处在于，体系反应温度为20℃。停止反应后，经后处理得到黄绿色固体为目标产物1(20mg,收率59％)。
实施例7
在氮气保护下，将四吡啶基卟啉锌-钌配合物1(2.5μmol)溶于20.0mL异丙醇中配成催化剂溶液。在氮气保护下，将底物苯乙酮(2.0mmol)、2mL催化剂溶液和17.6mL异丙醇的混合物在82℃搅拌5分钟。然后将0.4mL iPrOK的异丙醇溶液(0.05M)加入反应体系中。在指定的时间内，抽取0.1mL的反应液，并立即用0.5mL异丙醇稀释后做气相色谱分析。在所述条件下，苯乙酮几乎定量的还原为对应的醇产物，说明本发明的配合物可作为潜在的酮还原催化剂使用。
典型化合物表征数据
四吡啶基卟啉锌-钌配合物1，黄绿色固体。M.p.:>300℃,1H NMR(DMSO-d6,400MHz,23℃)δ9.01and 8.21(d each,8:8H),8.84(s,8H),8.09and 7.51(d each,4:4H,3-H and5-H),7.61(t,4H,4-H),7.44and7.32(d each,4:4H,5-H and 8-H),7.22and 7.08(m each,36:24H,Ph in PPh3),7.10and 7.00(m each,4:4H,6-H and 7-H),6.38(s,4H,4-H),2.68(s,12H,C3-CH3),2.53(s,12H,C5-CH3).δ159.81,156.72,155.05,152.1,151.49,150.5,150.1,145.96,146.52,144.54,143.2,136.0,135.86,132.91(d,o-C of PPh3),131.75(d,i-C PPh3),129.29(p-C of PPh3),127.8,127.64(d,m-C of PPh3),120.63,119.78,116.21,112.49,118.50,117.19,108.01,14.44(s,C3-CH3),14.16(s,C5-CH3).31P{1H}NMR(DMSO-d6,23℃)δ33.8.Anal.Calcd for C180H140Cl4N28P4Ru4Zn:C,63.15；H,4.32；N,11.45.Found:C,63.02；H,4.11；N,11.43.
Claims (9)
1.一种四吡啶基卟啉锌-钌配合物，其结构式1如下：
2.一种权利要求1所述四吡啶基卟啉锌-钌配合物的制备方法，其特征在于：利用配位不饱和的单核钌金属配合物2与四吡啶基卟啉锌3在溶剂中进行反应合成四吡啶基卟啉锌-钌配合物1；
四吡啶基卟啉锌3的结构如下：
四吡啶基卟啉锌-钌配合物1的合成路线如下述反应式所示：
3.按照权利要求2所述的制备方法，其特征在于：单核钌金属配合物2与四吡啶基卟啉锌3的反应溶剂为二氯甲烷、甲醇、乙醇和甲苯中的一种或者两种。
4.按照权利要求2所述的制备方法，其特征在于：单核钌金属配合物2与四吡啶基卟啉锌3的摩尔比范围为1:1-10:1。
5.按照权利要求2所述的制备方法，其特征在于：单核钌金属配合物2与四吡啶基卟啉锌3的反应温度为20 -110 oC，反应时间为1-24 h。
6.按照权利要求2所述的制备方法，其特征在于：反应气氛为氮气，压力条件为一个大气压。
7.按照权利要求2所述的制备方法，其特征在于：将反应体系减压浓缩后用二氯甲烷/正己烷的体积比= 1/3重结晶得到四吡啶基卟啉锌-钌配合物1。
8.一种权利要求1所述四吡啶基卟啉锌-钌配合物作为酮类化合物还原催化剂的应用。
9.按照权利要求8所述的应用，其特征在于：所述酮类化合物为芳香酮，脂肪酮。
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