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Metal complexes

A compound and metal atom technology, applied in the direction of gold organic compounds, osmium organic compounds, copper organic compounds, etc., can solve the problems that salts cannot deprotonate double carbene, limit, etc.

Active Publication Date: 2013-08-21
UDC IRELAND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] A disadvantage of the system described by Crabtree et al. is that the bisimidazole The salt cannot be deprotonated to give the biscarbene because the molecule rearranges under strongly basic reaction conditions and can no longer coordinate to the metal center
Therefore, the synthesis of metal complexes starting from free biscarbenes is not possible, which limits the choice of metal precursors

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0224] Example 1: 3,6-bis(chloromethyl)pyridazine

[0225]

[0226] 3,6-Dimethylpyridazine (6.60 g, 61.0 mmol) in anhydrous CHCl 3 (400ml) was heated to boiling under a protective gas atmosphere. Trichloroisocyanuric acid (12.3 g, 52.9 mmol) was then added in small portions over the course of one hour. In each case, the mixture foamed briefly and a brown suspension formed which was heated to reflux for an additional 2.5 hours. After cooling to room temperature, the light brown solid was separated through a filter (D4) and the filtrate was washed twice with 150 ml each of 0.2M aqueous NaOH and twice each with 200 ml water. Na 2 SO 4 After drying, the solvent was removed in vacuo to leave a brown oil, to which a small amount of pentane was added and the mixture was stored overnight at -30°C. The brown crystals formed were filtered and extracted with 50 ml anhydrous diethyl ether. The ether insoluble brown solid was discarded and the ether solution was evaporated to dryn...

Embodiment 2

[0234] Example 2: 3,6-bis(n-propylaminomethyl)pyridazine

[0235]

[0236] Under protective gas, n-propylamine (1.85ml, 1.33g, 22.6mmol) was added to 3,6-bis(chloromethyl)pyridazine (200mg, 1.13mmol) from Example 1 in anhydrous acetonitrile (5ml) in the solution. The brown solution was stirred overnight at room temperature, then evaporated to dryness. The residue was extracted twice with 5 ml each of a mixture of diethyl ether and acetonitrile (1:1 ) and once with diethyl ether (5 ml). The solution was evaporated in vacuo and the oily residue was recrystallized from diethyl ether at -30°C. The product was obtained as a yellow-brown solid (174 mg, 69%).

[0237] 1 H-NMR (CD 3 CN,400.13MHz):

[0238] δ=7.56(s,2H,4 / 5-H),3.99(s,4H,NCH 2 ),2.54(t, 3 J HH =7.1Hz,4H,NCH 2 -Pr),1.91(s,br,2H,NH),1.48(sext, 3 J HH =7.3Hz,4H,CH 2 -Pr),0.90(t, 3 J HH =7.4Hz,6H,CH 3 -Pr).

[0239] 13 C{ 1 H}-NMR (CD 3 CN,100.61MHz):

[0240] δ=162.7(C3 / 6), 127.5(C4 / 5), 54.3(NCH 2 ),...

Embodiment 9

[0244]Example 9: 3,6-bis(n-propylcarboxamidomethyl)pyridazine

[0245]

[0246] Under argon atmosphere, 3,6-bis(n-propylaminomethyl)pyridazine (1.60 g, 7.18 mmol) from Example 2 was added to formic acid (purity 99+%, 10 ml) and acetic anhydride (1.5 ml ) in the mixture. A small amount of gas evolved and a yellow-brown solution formed which was stirred at room temperature for 1.5 hours. Then 5 ml of water were added and the solution was evaporated to dryness in vacuo. The oily brown residue was extracted five times with 10 ml of diethyl ether each time. Using Na 2 SO 4 After drying, the ether solution was evaporated to dryness in vacuo to give the product as a light yellow oil in the form of its three isomers A, B and C, which was used without further purification (1.75 g, 88%) .

[0247] 1 H-NMR (CD 3 CN,400.13MHz):

[0248] (signals of isomers A, B and C assigned as best as possible)

[0249] δ=8.34, 8.33, (both s, 3H, CHO, A and B), 8.21, 8.20 (both s, 3H, CHO, ...

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Abstract

The present invention relates to bisimidazolium salts, to novel mono- and biscarbenes derived therefrom and to metal complexes which comprise corresponding mono- and biscarbenes as ligands, to a process for the preparation of the bisimidazolium salts according to the invention, of the mono- and biscarbenes according to the invention and of the metal complexes according to the invention, and to the use of the bisimidazolium salts according to the invention, of the mono- and biscarbenes according to the invention and to the use of the metal complexes according to the invention.

Description

technical field [0001] The present invention relates to bis-imidazole Salts, to novel monocarbenes and dicarbenes derived therefrom, to metal complexes comprising the corresponding monocarbenes and biscarbenes as ligands, to the use in the preparation of bisimidazoles according to the invention Processes for salts, monocarbenes and dicarbenes according to the invention and metal complexes according to the invention, and to bis-imidazoles according to the invention Salts, uses of the monocarbenes and dicarbenes according to the invention, and relate to the use of the metal complexes according to the invention. Background technique [0002] imidazole salt and bisimidazole Salts and methods for their preparation are known in the literature. These are compounds that are precursors of N-heterocyclic carbenes and their metal complexes. The carbene itself can be used as a nucleophilic organocatalyst. Metal complexes of N-heterocyclic carbenes can be used as metal catalys...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07F1/08C07F1/10C07F1/12H01L51/00H10K99/00
CPCC07F1/00C07F11/00C07F13/00C07F15/002C07F15/0033C07F15/0086Y02E10/549H10K85/346H10K85/342H10K50/11H10K2101/10C07F15/00C09K11/06H10K50/00H10K85/361H10K85/341H10K85/348
Inventor 多里斯·孔茨韦尔娜·吉尔兹
Owner UDC IRELAND
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