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Method for preparing epoxide through induction of visible light

A technology of epoxy and visible light, applied in chemical instruments and methods, chemical/physical processes, organic compounds/hydrides/coordination complex catalysts, etc., can solve rare problems and achieve mild and good reaction conditions Application and development value, good environmental friendliness effect

Active Publication Date: 2018-05-29
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although there are many reports on epoxidation in the literature, there are not many literatures and patents using molecular oxygen as the oxidizing agent.

Method used

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  • Method for preparing epoxide through induction of visible light
  • Method for preparing epoxide through induction of visible light
  • Method for preparing epoxide through induction of visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of 1,3-diphenyl-2,3-epoxy-1-propanone

[0036] Weigh 1,3-diphenyl-2-propen-1-one (84.69mg, 0.4mmol) and tetraphenylporphyrin 1.62mg (0.0025mmol) into a 20ml single-port reaction tube, add toluene 2ml, IIIa- 1 (243 mg, 1.2 mmol). At 10°C, under an oxygen atmosphere, irradiate with a 10W LED light strip, and stir the reaction. After 96h, the reaction was completed, column separation, rotary evaporation, and vacuum drying gave the epoxidized product (35.34mg, 38% yield) 1 H NMR (400MHz, Chloroform-d) δ8.03 (t, J = 1.3Hz, 1H), 8.01 (d, J = 1.5Hz, 1H), 7.66–7.59 (m, 1H), 7.50 (m, J = 8.4,7.1Hz,2H),7.40(m,J=5.8,5.1,3.5Hz,5H),4.31(d,J=1.8Hz,1H),4.08(d,J=1.9Hz,1H).

Embodiment 2

[0037] Example 2: Preparation of 1,3-diphenyl-2,3-epoxy-1-propanone

[0038] Weigh 1,3-diphenyl-2-propen-1-one (82.98mg, 0.4mmol) and tetraphenylporphyrin (1.52mg, 0.0025mmol) into a 20ml single-port reaction tube, add toluene 2ml, IIIa -2 (556.8mg, 4mmol), at 10°C, under an oxygen atmosphere, irradiated with a 10W LED light strip, and stirred for reaction. After 144 hours, the reaction was completed, and the epoxidized product (58.74 mg, 66% yield) was obtained by column separation, rotary evaporation, and vacuum drying.

Embodiment 3

[0039] Example 3: Preparation of 1,3-diphenyl-2,3-epoxy-1-propanone

[0040] Weigh 1,3-diphenyl-2-propen-1-one (83.28mg, 0.4mmol) and tetraphenylporphyrin (1.50mg, 0.0025mmol) into a 20ml single-port reaction tube, add toluene 2ml, IIIa -2 (556.8mg, 4mmol), at 10°C, under an oxygen atmosphere, irradiated with a 10W LED light strip, and stirred for reaction. After 144 hours, the reaction was completed, and the epoxidized product (55.38 mg, 62% yield) was obtained by column separation, rotary evaporation, and vacuum drying.

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Abstract

The invention belongs to the technical field of organic synthesis and provides a method for preparing an epoxide through induction of visible light. The method comprises the following step: under thecondition that the visible light and a photosensitizer exist, by taking oxygen or air as an oxygen source or an oxidizing agent and taking a synthesized amidine derivative as a catalyst, performing areaction at the temperature of -40-50 DEG C for 36h-192h, so that olefin is directly oxidized into the corresponding epoxide. The method is mild in reaction conditions, and the yield is as high as 94%or above, therefore, the method has good development value and application prospect.

Description

technical field [0001] The invention belongs to the field of photocatalytic organic synthesis, and relates to a method for preparing epoxides by epoxidation of olefins participated in by formamidine derivatives under the irradiation of visible light. Background technique [0002] Photoinduced organocatalysis is one of the very challenging and promising organic synthesis methods in the 21st century. Visible light-induced organocatalysis is a very hot field and has received extensive attention. Epoxides are an important class of organic synthesis intermediates or structural units, widely used in organic synthesis, medicine, materials and other fields, such as α, β-epoxy alcohols, β-amino alcohols, halogenated alcohols, etc. Since Katsuki and Sharpless first used tartrate to catalyze the asymmetric epoxidation of allyl alcohol in 1980 (JACS.1980, 102(18), 5974-5976), olefin epoxidation has become a major research hotspot. From the perspective of catalysts and oxidants, olefin...

Claims

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Application Information

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IPC IPC(8): C07D301/06C07D303/32B01J31/02
CPCC07D301/06C07D303/32B01J31/0245B01J35/39
Inventor 孟庆伟武玉峰刘广志唐晓飞尹航赵静喃杨帆冯世豪李根于宗义
Owner DALIAN UNIV OF TECH
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