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Method for preparing 2-iodine amyl -2-ene-1,4-diketone derivative by adopting visible light catalysis

A catalytic preparation and visible light technology, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as poor regioselectivity, low product yield, and narrow range of reaction substrates. Gentle, good yield, high selectivity effect

Active Publication Date: 2017-08-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process allows for easy access into various types of compounds that can be used as starting materials or intermediates during chemical reactions without causing harmful environmental impact. It also provides excellent yields due to its use of visible light technology and does away from any contamination concerns associated therewith.

Problems solved by technology

The technical problem addressed in this patented text relating to chemistry involving certain types of compound has been finding ways to make these compounds more efficiently or with better results compared to existing methods like condensations between α-,β-unsaturated ketenoids and unsymmetrical alcohols.

Method used

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  • Method for preparing 2-iodine amyl -2-ene-1,4-diketone derivative by adopting visible light catalysis
  • Method for preparing 2-iodine amyl -2-ene-1,4-diketone derivative by adopting visible light catalysis
  • Method for preparing 2-iodine amyl -2-ene-1,4-diketone derivative by adopting visible light catalysis

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Experimental program
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Effect test

Embodiment 1

[0045] In a Schlenk tube, add NaI (60.0 mg, 0.4 mmol), Ir (ppy) in sequence 3 (1.3mg, 0.002mmol), 5-phenylpenta-3,4-dien-2-one (31.6mg, 0.2mmol), C 4 f 9 I (103.8 mg, 0.3 mmol) and toluene (6 ml) were connected to an oxygen atmosphere, and stirred at room temperature for 10 h under the irradiation of white light from a 45W energy-saving lamp. After the reaction was completed, the reaction solution was washed twice with water, and the water phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, spin-dried by a rotary evaporator, and then purified by silica gel column chromatography to obtain the light yellow target product 2-iodo-1-phenylpent-2-ene-1,4-dione. Yield 48%, purity ≥ 98%. Product characterization data are as follows: 1H NMR (500MHz, CDCl3) δ7.93 (dt, J = 8.5, 1.5Hz, 2H), 7.63–7.58 (m, 1H), 7.52–7.46 (m, 2H), 7.19 (s, 1H), 2.19(s, 3H). 13 C NMR (126MHz, CDCl 3 )δ193.74, 192.64, 139.95, 133.98, 131.96, 129.19, 128.90, 114.24, 29.79; HRMS ...

Embodiment 2

[0048] In a Schlenk tube, sequentially add NH 4 I (58.0 mg, 0.4 mmol), Ir (ppy) 3 (1.3mg, 0.002mmol), 5-phenylpenta-3,4-dien-2-one (31.6mg, 0.2mmol), C 4 f 9 I (103.8 mg, 0.3 mmol) and toluene (6 ml) were connected to an oxygen atmosphere, and stirred at room temperature for 10 h under the irradiation of white light from a 45W energy-saving lamp. After the reaction was completed, the reaction solution was washed twice with water, and the water phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, spin-dried by a rotary evaporator and purified by silica gel column chromatography to obtain the light yellow target product (Z)-2-iodo-1-phenylpent-2-ene-1,4 - Diketone, yield 49.6%, purity ≥ 98%.

Embodiment 3

[0050] In a Schlenk tube, add KI (66.4 mg, 0.4 mmol), Ir (ppy) in sequence 3 (1.3mg, 0.002mmol), 5-phenylpenta-3,4-dien-2-one (31.6mg, 0.2mmol), C 4 f 9 I (103.8 mg, 0.3 mmol) and toluene (6 ml) were connected to an oxygen atmosphere, and stirred at room temperature for 10 h under the irradiation of white light from a 45W energy-saving lamp. After the reaction was completed, the reaction solution was washed twice with water, and the water phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, spin-dried by a rotary evaporator, and then purified by silica gel column chromatography to obtain the light yellow target product 2-iodo-1-phenylpent-2-ene-1,4-dione. Yield 63%, purity ≥ 98%.

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Abstract

The invention discloses a method for preparing a 2-iodine amyl -2-ene-1,4-diketone derivative by adopting visible light catalysis. The method comprises the steps of adding allene, perfluorobutyl iodide, an additive and a photocatalyst as shown in a formula (I) to an organic solvent at the molar ratio of 1:(1-2):(1-2):(0.005-0.1), stirring under the conditions of an oxygen atmosphere, visible light illumination, room temperature and ordinary pressure for 10-20h, carrying out post-treatment on a reaction liquid to obtain a 2-iodine amyl -2-ene-1,4-diketone derivative as shown in a formula (II), wherein the additive is NaI, NH4I or KI; the organic solvent is ethanol, dichloromethane, benzene, methylbenzene, tetrahydrofuran or acetonitrile; the photocatalyst is selected from one of the following components: Ir(ppy)3, Eosin Y, Rose Bengal, [Ir(dF-CF3-ppy)2(dtbbpy)]PF6, [Ir(ppy)2(tbbpy)]PF6, Ru(bpy)3(BF4)2. The method is mild in reaction condition, simple in operation, high in selectivity and good in yield; a substituent group can be expanded; and visible light catalysis is adopted, so that the method has the characteristics of being free of pollution and environment-friendly. The formulas are as shown in the specification.

Description

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Claims

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Application Information

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Owner ZHEJIANG UNIV OF TECH
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