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Photo-oxidation reduction catalysis method

A technology of photooxidation and compounds, applied in organic chemical methods, chemical instruments and methods, organic chemistry, etc.

Active Publication Date: 2021-09-14
SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite the remarkable research progress described above, little attention has been paid to the generation of alkyl radicals in a precisely controlled manner using common, environmentally benign chemical feedstocks

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] A preparation method of 2-(1,2-diphenylethyl) malononitrile compound (structural formula shown in formula 1 below):

[0085]

[0086] Photocatalyst Mes-Acr-PhBF 4 (0.01 mmol, 4.6 mg) and capture reagent benzylmalononitrile (0.4 mmol, 61.7 mg) were weighed into oven-dried 8 mL vials equipped with magnetic star marking rods. Anhydrous acetonitrile (1 mL) was added followed by the linear tertiary alcohol (2-methyl-1-phenyl-2-propanol) (0.2 mmol). The reaction vessel was degassed, backfilled with argon, and then placed in a SynLED 4x4 photoreactor (SynLED discoverTM 450nm, designed and manufactured by Shenzhen SynLED Tech. Ltd). The progress of the reaction was monitored by TLC. After completion, the reaction mixture was concentrated and purified by silica gel flash column chromatography to obtain the target product in 85% yield.

[0087] Correlation characterization analysis, the result is 1 H NMR (500MHz, Chloroform-d) δ7.47–7.38(m,5H),7.35(dd,J=8.1,6.4Hz,2H),7.32–...

Embodiment 2

[0089] A preparation method of 2-(1,3-diphenylpropyl) malononitrile compound (structural formula shown in formula 2 below):

[0090]

[0091] The linear tertiary alcohol is 3-methyl-1-phenyl-3-pentanol, and the capture reagent is benzallyl dinitrile; other preparation methods are the same as in Example 1, and the yield is 81%.

[0092] Correlation characterization analysis, the result is 1 H NMR (500MHz, Chloroform-d) δ7.51–7.40(m,3H),7.38–7.28(m,4H),7.26–7.22(m,1H),7.14–7.07(m,2H),3.86(d ,J=6.2Hz,1H),3.20(dt,J=10.2,5.7Hz,1H),2.66(ddd,J=13.6,8.3,5.2Hz,1H),2.48(dt,J=13.8,8.2Hz, 1H),2.43–2.29(m,2H). 13 C NMR (126MHz, Chloroform-d) δ139.90, 136.24, 129.48, 129.12, 128.73, 128.38, 128.05, 126.57, 111.81, 111.77, 45.64, 33.53, 32.77, 30.37. HRMS (ESI-TOF) calculated for C 18 h 16 N 2 (M+Na + ): 283.1206, found: 283.1206. This result further confirms that the molecular structure of the product is just like the molecular structure 2 above.

Embodiment 3

[0094] A preparation method of 2-(2-(4-isobutylphenyl)-1-phenylpropyl) malononitrile compound (structural formula shown in formula 3 below):

[0095]

[0096] Linear tertiary alcohol is 3-(4-isobutylphenyl)-2-methylbutan-2-alcohol, and trapping reagent is benzallyl dinitrile; Others are identical with the preparation method of embodiment 1, and productive rate is 84%, dr is 1:1.

[0097] Correlation characterization analysis, the result is isomer 1: 1 H NMR (500MHz, Chloroform-d) δ7.31–7.22(m,3H),7.01–6.90(m,4H),6.84(d,J=7.9Hz,2H),4.07(d,J=8.1Hz, 1H), 3.49(p, J=7.0Hz, 1H), 3.42(t, J=7.8Hz, 1H), 2.40(dd, J=7.2, 1.8Hz, 2H), 1.80(dp, J=13.5, 6.8 Hz,1H),1.43(d,J=6.9Hz,3H),0.86(dd,J=6.6,1.5Hz,6H). 13 C NMR (126MHz, Chloroform-d) δ140.84, 137.54, 134.88, 129.12, 128.85, 128.57, 128.46, 127.87, 112.58, 112.03, 52.76, 44.95, 41.25, 30.15, 27.48, 22.38, 192.92

[0098] Isomer 2: 1 H NMR (400MHz, Chloroform-d) δ7.58–7.42 (m, 5H), 7.30 (d, J = 7.9Hz, 2H), 7.23 (d, J = 8.1Hz, 2H),...

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Abstract

The invention relates to the technical field of synthetic chemistry, in particular to a photo-oxidation reduction catalysis method. The photo-oxidation reduction catalysis method comprises the steps of providing a linear tertiary alcohol compound and a free radical capture reagent; and carrying out catalytic reaction on the linear tertiary alcohol compound and the free radical capture reagent under the condition of a photocatalyst. According to the novel alcohol-extended alkyl radical chemistry method provided by the invention, under the condition of a photocatalyst, linear tertiary alcohol induces carbon-carbon bond breakage through single-electron oxidation to generate alkyl radicals, and then the alkyl radicals are captured by a radical capture reagent to react to obtain various products; and according to the photo-oxidation reduction catalysis method, the production cost for preparing the capture product is remarkably reduced, and the designability and the application prospect of the product are greatly expanded.

Description

technical field [0001] The application belongs to the technical field of synthetic chemistry, and in particular relates to a photoredox catalytic method. Background technique [0002] In recent years, with the understanding of the photocatalytic mechanism and the development of photoredox catalysts, visible light-promoted photoredox catalysis (photoredox catalysis) has been developed rapidly and has made remarkable achievements, completely changing the modern free radical Chemical. [0003] Alkyl radicals have been studied to play an indispensable role in the development of novel synthetic methods under photo / electrochemical catalysis. Typically, alkyl radical precursors undergo single-electron transfer with the help of photoredox catalysts to generate transient alkyl radicals that can participate in various bond-forming processes in a chemical and stereoselective manner, and a large number of The precursors of alkyl radicals, which have a built-in redox group, can narrow ...

Claims

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Application Information

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IPC IPC(8): C07C255/33C07C255/37C07C255/35C07C253/30C07C69/612C07C67/347C07C317/14C07C315/04C07D309/04C07D215/04C07D241/12C07D277/64C07D213/16C07D213/127C07D239/26C07D277/56C07D473/40C07D453/04C07B61/00
CPCC07C253/30C07C67/347C07C315/04C07D309/04C07D215/04C07D241/12C07D277/64C07D213/16C07D213/127C07D239/26C07D277/56C07D473/40C07D453/04C07B61/02C07C2601/14C07C2603/74C07C255/33C07C255/37C07C255/35C07C69/612C07C317/14
Inventor 黄湧陈杰安廖柯
Owner SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT
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