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Coordination compound with half-sandwich iridium structure and solid-phase synthesis method

A coordination compound and solid-phase synthesis technology, applied in chemical instruments and methods, organic chemistry, metallocene, etc., can solve problems such as environmental impact, large energy consumption, and harsh reaction conditions

Pending Publication Date: 2021-05-11
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The semi-sandwich structure iridium complex is a typical organometallic coordination compound. The usual synthesis method is completed under the Schlenk technical conditions of anhydrous and oxygen free. Under this condition, the water in the solvent should be strictly removed. It is completed under the protection of inert gas, the reaction conditions are harsh, it needs to consume a lot of energy and has a certain impact on the environment, and requires high capital and manpower investment

Method used

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  • Coordination compound with half-sandwich iridium structure and solid-phase synthesis method
  • Coordination compound with half-sandwich iridium structure and solid-phase synthesis method
  • Coordination compound with half-sandwich iridium structure and solid-phase synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Complex 1a of Half-Sandwich Iridium and Octahydroxyquinoline Derivatives:

[0047]

[0048] Weigh [Cp*Ir(μ-Cl)Cl] 2 (0.10mmol) placed in a quartz mortar, add octahydroxyquinoline derivative 1 (0.2mmol), then add K 2 CO 3 (0.2mmol), then add 5 drops of CH 2 Cl 2 (0.10 mL). After grinding with an agate mortar for 40 min at room temperature (25°C), add 5 mL of CH 2 Cl 2 Dissolve and filter 2-3 times to remove insoluble matter. Remove most of the CH under reduced pressure using a rotary evaporator 2 Cl 2 , separated by column chromatography (n-hexane:isopropanol=3:1) to obtain the complex 1a of half-sandwiched iridium and octahydroxyquinoline derivatives (90% yield).

[0049] Characterized by proton nuclear magnetic spectrum, carbon spectrum, mass spectrum and infrared. 1 H NMR (400MHz, CDCl 3 , ppm): δ=10.43(s, 1H), 8.11(d, J=8Hz, 1H), 7.92(d, J=8Hz, 1H), 7.51(t, J=16Hz, 1H), 7.04(d, J=8Hz,1H),6.82(d,J=8Hz,1H),1.63(s,15H). 13 C NMR (100MHz, CDC...

Embodiment 2

[0051] Synthesis of Complex 2a of Half-Sandwich Iridium and Octahydroxyquinoline Derivatives:

[0052]

[0053] Weigh [Cp*Ir(μ-Cl)Cl] 2 (0.10mmol) is placed in quartz mortar, adds octahydroxyquinoline derivative 2 (0.2mmol), then adds K 2 CO 3 (0.2mmol), then add 5 drops of CH 2 Cl 2 (0.10 mL). After grinding with an agate mortar for 40 min at room temperature (10°C), add 5 mL of CH 2 Cl 2 Dissolve and filter 2-3 times to remove insoluble matter. Remove most of the CH under reduced pressure using a rotary evaporator 2 Cl 2 , separated by column chromatography (n-hexane:isopropanol=3:1) to obtain the complex 2a of half-sandwiched iridium and octahydroxyquinoline derivatives (88% yield).

[0054] Characterized by proton nuclear magnetic spectrum, carbon spectrum, mass spectrometry and infrared, respectively see Figure 1-Figure 4 . 1 H NMR (400 MHz, CDCl 3 , ppm): δ=8.04(d, J=16Hz, 1H), 7.92(d, J=12Hz, 1H), 7.74(d, J=8Hz, 1H), 7.65(d, J=8Hz, 2H), 7.43(t, J=16Hz, ...

Embodiment 3

[0056] Synthesis of complex 3a of half-sandwich iridium and octahydroxyquinoline derivatives:

[0057]

[0058] Weigh [Cp*Ir(μ-Cl)Cl] 2 (0.10mmol) placed in a quartz mortar, add octahydroxyquinoline derivative 3 (0.2mmol), then add K 2 CO 3 (0.2mmol), then add 5 drops of CH 2 Cl 2 (0.10 mL). After grinding with an agate mortar for 40 min at room temperature (18°C), add 5 mL of CH 2 Cl 2 Dissolve and filter 2-3 times to remove insoluble matter. Remove most of the CH under reduced pressure using a rotary evaporator 2 Cl 2 , separated by column chromatography (n-hexane:isopropanol=3:1) to obtain the complex 3a of half-sandwiched iridium and octahydroxyquinoline derivatives (92% yield).

[0059] Characterized by proton nuclear magnetic spectrum, carbon spectrum, mass spectrum and infrared. 1 H NMR (400MHz, CDCl 3 , ppm): δ=8.04(d, J=16Hz, 1H), 7.92(d, J=8Hz, 1H), 7.70(d, J=8Hz, 1H), 7.56(d, J=8Hz, 2H), 7.39(d, J=8Hz, 2H), 7.30(t, J=8Hz, 1H), 7.26(d, J=8Hz, 1H), 6.92(d...

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Abstract

The invention discloses a coordination compound with a half-sandwich iridium structure and a solid-phase synthesis method. The structural formula of the compound is a formula 1a, a formula 2a or a formula 3a, X in the formula 3a is halogen, and the substitution position is ortho-position, meta-position or para-position. The method comprises the step that [Cp*Ir([mu]-Cl)Cl]2 and an octahydroxyquinoline derivative react in a grinding mode in the presence of a very small amount of solvent and alkali. According to the synthesis method, solid-phase synthesis is performed in a grinding manner, so that the use of a solvent is greatly reduced, inert gas protection can be avoided, the cost is low, the operation is simple, the environmental pollution is small, industrial application is facilitated, and in addition, the synthesis method also has relatively high yield.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, in particular to a coordination compound with a semi-sandwich iridium structure and a solid phase synthesis method. Background technique [0002] Complexes of iridium and rhodium with a semi-sandwich structure have unique chemical stability, redox properties, and rich catalytic properties for organic reactions. The semi-sandwich structure of iridium and rhodium complexes is the key research content of inorganic chemistry, material chemistry and coordination chemistry, and has gradually become a very active field in modern chemical research. Coordination compounds with semi-sandwich structure iridium play an important role in organic catalysis, carbon dioxide reduction, water splitting, etc. Therefore, it is a very important research content to synthesize and explore the synthesis and application of a series of organometallic coordination compounds with semi-sandwich structure. The s...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 贾卫国支雪婷盛恩宏
Owner ANHUI NORMAL UNIV
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