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

A technology of compounds and cyclometals, applied in the field of heteronuclear palladium-gold bicyclic metal compounds, can solve problems such as heteronuclear palladium-gold bicyclic metal compounds, etc., and achieve a wide range of reaction substrates, strong thermal stability and air stability , the effect of mild reaction conditions

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

So far, there have been no reports on the synthesis of heteronuclear palladium-gold bicyclic metal compounds and their use as bimetallic catalysts to catalyze the reaction of ortho-N-substituted halobenzenes and alkynes, and the synthesis and preparation of 1,2-substituted indoles

Method used

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

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Effect test

Embodiment 1

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

[0026]

[0027]

Embodiment 2

[0029] Preparation of heteronuclear triphenylphosphine palladium gold bicyclic metal compound (1): Add 1.3mmol mononuclear palladium compound (triphenylphosphine mononuclear palladium compound containing bromine atom) in a 50ml three-necked flask equipped with a stirring reflux device ), 1mmol mononuclear cyclic gold compound (mononuclear cyclic gold compound containing boronate group), 2.0mmol potassium carbonate, 20ml anhydrous toluene, stirred and reacted at 110°C for 12h under nitrogen atmosphere, filtered, evaporated Dichloromethane (CH 2 Cl 2 ) recrystallized to obtain the yellow product (1) with a yield of 91.2%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1 HNMR: δ=8.60(d,1H,Ph-H),8.57(d,1H,Ph-H),8.10(d,2H,Ph-H),7.65-7.41(m,11H,Ph-H), 7.10-7.36 (m, 12H, Ph-H).

[0030] The specific structures of mononuclear cyclopalladium compounds and mononuclear cyclogold compounds are shown in Table 1, the same below.

Embodiment 3

[0032] Preparation of heteronuclear triisopropylphosphine palladium gold bicyclic metal compound (3): Add 1mmol mononuclear palladium compound (triisopropylphosphine mononuclear palladium containing chlorine atom) in a 50ml three-neck flask equipped with a stirring reflux device Compound), 1mmol mononuclear cyclogold compound (mononuclear borate group-containing mononuclear cyclogold compound), 2.5mmol sodium carbonate, 20ml anhydrous tetrahydrofuran, stirred at 80°C for 20h under nitrogen atmosphere, filtered, evaporated After removing the solvent, it was recrystallized with CH2Cl2 to obtain the red product (3) with a yield of 92.6%. Gained product is carried out nuclear magnetic resonance analysis, data is as follows: 1HNMR: δ=8.57(d,1H,Ph-H),8.53(d,1H,Ph-H),8.10(d,2H,Ph-H),7.60-7.47(m,8H,Ph-H), 7.11(m,1H,Ph-H),2.36(s,3H,CH 3 ),2.06(m,3H,CH),1.10(d,18H,CH 3 ).

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Abstract

The invention provides a heteronuclear palladium gold bicyclo metal compound as well as a preparation method and an application of the compound, belonging to the field of organic synthesis. The technical scheme is as follows: the heteronuclear palladium 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, R1 and R2 are H or straight-chain alkyl in which C is equal to 1-10. The preparation method comprises the following synthesis steps of: adding mononuclear cyclo-palladium compound containing halogen atoms, mononuclear cyclo-gold compound containing borate ester and alkali in an organic solvent; under the protection of inert gas, carrying out heating reflux; and after the reaction is finished, filtering, drying by distillation, and re-crystallizing, so as to obtain the compound. According to the invention, the heteronuclear palladium gold bicyclo metal compound also is used as a catalyst to catalyze the reaction of O-N-substituted halogeno benzene and alkyne so as to synthesize 1,2-substituted indole, and the reaction is economic and efficient, so that the compound has important application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a group of heteronuclear palladium-gold bicyclic metal compounds, as well as the preparation method and application of the compounds. Background technique [0002] Indoles are important organic raw materials and chemicals that have attracted great attention in recent years. Indole compounds can not only synthesize dyes and spices, but also be used as plant auxins and active alkaloids to treat various diseases, so they have a very wide range of important uses in industry, agriculture and medicine. With the in-depth understanding of the use of indole compounds, more and more researches have been done on their synthesis methods. The acid-catalyzed Fischer synthesis method is traditionally used, but it has the disadvantages of low yield and poor regioselectivity. In addition, this method needs to use phenylhydrazine and its derivatives as raw materials, which are easily o...

Claims

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Application Information

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IPC IPC(8): C07F19/00B01J31/22C07D209/08
Inventor 徐晨娄新华李红梅王志强李仕辉付维军
Owner LUOYANG NORMAL UNIV
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