Ferrocenyl-containing arylamine compound and synthesis method thereof

A synthesis method and compound technology, applied in chemical instruments and methods, metallocenes, organic chemistry, etc., to achieve high atom economy, easy access to reagents, and simple synthesis of substrates

Active Publication Date: 2020-09-15
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are many methods for synthesizing arylamine derivatives, but basically all of them require certain conditions to comp

Method used

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  • Ferrocenyl-containing arylamine compound and synthesis method thereof
  • Ferrocenyl-containing arylamine compound and synthesis method thereof
  • Ferrocenyl-containing arylamine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A ferrocenyl-arylamine-containing compound, the structural formula of the ferrocenyl-arylamine-containing compound is:

[0040]

[0041] The synthetic method of above-mentioned ferrocenyl arylamine compound comprises the following steps:

[0042] Prepare the ingredients first:

[0043] (s)-(4-isopropyloxazolin-2-yl)ferrocene, TCI (Shanghai) Chemical Industry Development Co., Ltd.;

[0044] 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, TCI (Shanghai) Chemical Industry Development Co., Ltd.;

[0045] The specific synthesis method is:

[0046] At 60°C, 1.2mmol of (s)-(4-isopropyloxazolin-2-yl)ferrocene and 1.0mmol of trifluoromethanesulfonic acid-2-(trimethylsilyl) Phenyl ester, 2.0mmol of cesium fluoride as base and 2.0mmol of 18-crown-6-ether were reacted in 2mL of toluene solvent for 12 hours to obtain the crude product containing ferrocenyl arylamine compound; the prepared ferrocene-containing The crude product of the arylamine compound was washed with...

Embodiment 2

[0051] A ferrocenyl-arylamine-containing compound, the structural formula of the ferrocenyl-arylamine-containing compound is:

[0052]

[0053] The above-mentioned synthetic method containing ferrocenyl arylamine compound comprises the following steps:

[0054] Prepare ingredients:

[0055] (s)-(4-isopropyloxazolin-2-yl)ferrocene, TCI (Shanghai) Chemical Industry Development Co., Ltd.;

[0056] Trifluoromethanesulfonic acid-4-methyl-2-(trimethylsilyl)phenyl ester, TCI (Shanghai) Chemical Industry Development Co., Ltd.;

[0057] Specific synthesis method:

[0058] At 60°C, (s)-(4-isopropyloxazolin-2-yl)ferrocene 1.2mmol, trifluoromethanesulfonic acid-4-methyl-2-(trimethylsilyl ) 1.0mmol of phenyl ester, 2.0mmol of cesium fluoride as base and 2.0mmol of 18-crown-6-ether were reacted in 2mL toluene solvent for 12 hours to obtain the crude product of ferrocenyl arylamine compound; The crude iron-based arylamine compound was washed with water, extracted with ethyl acetate, s...

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Abstract

The invention provides a ferrocenyl-containing arylamine compound and a synthesis method thereof. A trifluoromethanesulfonic acid-2-(trimethylsilyl) phenyl ester compound is used as a benzyne precursor, cesium fluoride is used as an alkali, 18-crown-6-ether is used as a phase transfer catalyst, and a ferrocenyl arylamine structural unit is efficiently constructed through a one-pot reaction under the condition of no additional metal catalyst. The reaction overcomes the defects that a transition metal or noble metal catalyst needs to be added in the conventional reaction, the requirements on a substrate and reaction conditions are harsh and the like, the reaction is simple in substrate synthesis, reagents are easy to obtain, target molecules are obtained simply and quickly with high atom economy, and a brand-new way is provided for developing the ferrocenyl-containing arylamine compound.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to a ferrocenyl-containing arylamine compound and a synthesis method thereof. Background technique [0002] Amines and their derivatives are important chemical intermediate products with a long production history, large output and wide application. Aromatic amines and their derivatives are widely used in chemical industry, medicine, agrochemicals, photographic chemicals, additives, surfactants and polymer production, and are important organic raw materials. N atoms on arylamine compounds have strong electron-donating ability and good electronpositivity, so these compounds generally have high hole injection and migration abilities. As important organic synthesis intermediates, arylamine compounds can be used in the preparation and application of organic dyes, nonlinear optical materials, liquid crystal materials, optical information storage materials and optical switch m...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02Y02P20/584
Inventor 鲍丽胡益民
Owner ANHUI NORMAL UNIV
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