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Heteronuclear iridium gold bicyclo metal compound as well as preparation method and application of compound

A compound and cyclic metal technology, applied in the field of heteronuclear iridium bicyclic metal compounds, the preparation of such compounds, achieves the effects of strong thermal stability and air stability, mild reaction conditions and high yield

Inactive Publication Date: 2013-04-03
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Up to now, there is no synthesis of heteronuclear iridium-gold bicyclic metal compound and its use as a bimetallic catalyst to catalyze the three-component coupling reaction of aryl benzyl alcohol, arylamine and alkyne to synthesize and prepare multi-substituted quinoline compounds

Method used

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  • Heteronuclear iridium gold bicyclo metal compound as well as preparation method and application of compound
  • Heteronuclear iridium gold bicyclo metal compound as well as preparation method and application of compound
  • Heteronuclear iridium gold bicyclo metal compound as well as preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A group of heteronuclear iridium gold bicyclic metal compounds, the general formula is The specific structure can be:

[0026]

[0027]

[0028]

Embodiment 2

[0029] Example 2 Preparation of heteronuclear trimethylphosphine-iridium-gold bicyclic metal compound (1): Add 1.2 mmol of mononuclear iridium compound (trimethylphosphine mononuclear ring iridium compound), 1mmol mononuclear ring gold compound (mononuclear ring gold compound containing boronate group), 0.05mmol palladium chloride, 1.5mmol cesium carbonate, 20ml anhydrous dioxane, temperature 110℃ , stirred and reacted for 10h under nitrogen atmosphere, filtered, evaporated the solvent, and then used dichloromethane (CH 2 Cl 2 ) solvent recrystallization to obtain the yellow product (1) with a yield of 88.5%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1H NMR: δ=8.62(d,1H,Ph-H),8.58(d,1H,Ph-H),8.12(d,2H,Ph-H),7.68-7.39(m,8H,Ph-H) ,7.11-6.96(m,2H,Ph-H),0.96(s,18H,CH 3 ).

Embodiment 3

[0030] Example 3 Preparation of heteronuclear triphenylphosphine iridium gold bicyclic metal compound (3): Add 2 mmol of mononuclear iridium compound (triphenylphosphine mononuclear ring containing bromine atom iridium compound), 1mmol mononuclear cyclic gold compound (mononuclear cyclic gold compound containing boronate group), 0.2mmol palladium chloride, 5mmol potassium carbonate, 20ml anhydrous toluene, stirring at 110°C under nitrogen atmosphere Filter after reacting for 8h, dichloromethane (CH 2 Cl 2 ) solvent recrystallization, the yellow product (3) was obtained with a yield of 89.2%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 H NMR: δ=8.60(d,1H,Ph-H),8.57(d,1H,Ph-H),8.10(d,2H,Ph-H),7.65-7.41(m,20H,Ph-H) ,7.10-7.36(m,19H,Ph-H),2.35(s,3H,CH 3 ).

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Abstract

The invention provides a heteronuclear iridium gold bicyclo metal compound as well as a preparation method and an application of the compound, and belongs to the field of organic synthesis. The technical scheme is as follows: the heteronuclear iridium gold bicyclo metal compound has a general formula as shown in the specification, wherein in the formula, X, X1, Y and Y1 are C atoms or N atoms, the same atoms are used when X is different from Y, and the same atoms are used when X1 is different from Y, Z and Z1 are selected from Cl<-1>, Br<-1> and I<-1>, L is tertiary phosphine ligand or N-heterocyclic carbenes ligand, R and R1 are H or straight-chain alkyl in which C is equal to 1-10. the preparation method comprises the synthesis steps of: adding a mononuclear cyclo-iridium compound, a mononuclear cyclo-gold compound, palladium salt and alkali in an organic solvent; under the protection of N2, carrying out heating reflux; and after the reaction is finished, filtering, drying by distillation, and re-crystallizing, so as to obtain the heteronuclear iridium gold bicyclo metal compound. According to the invention, the bicyclo metal compound is used as a catalyst to catalyze aryl benzyl alcohol, arylamine and alkyne to carry out three-component coupling reaction, so as to synthesize poly-substitution quinoline compound in one step, and the reaction is high in yield and wide in application prospect.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a class of heteronuclear iridium-gold bicyclic metal compounds, and also relates to a preparation method and application of the compounds. Background technique [0002] Quinoline and its derivatives are important heterocyclic compounds, which are widely used in industrial production such as medicine, health products, and pesticides. Many quinoline derivatives have biological and pharmacological activities such as sterilization, antibacterial, anti-allergic, and anti-tumor. With social development and people's medical needs, the demand for quinoline derivatives in related industries is also increasing. Industrially, quinoline and its derivatives were first extracted from coal tar. This technical route is complex and the product range is limited. Some important quinoline derivatives cannot be obtained by this method. Catalytic chemical synthesis is also a traditional me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F19/00B01J31/22C07D215/04C07D215/14C07D215/18
Inventor 徐晨李红梅王志强娄新华付维军
Owner LUOYANG NORMAL UNIV
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