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A method for the continuous preparation of chiral α-hydroxy-β-dicarbonyl compounds by visible light-catalyzed molecular oxygen oxidation via a microreactor

A technology of dicarbonyl compounds and microreactors, which is applied in the field of flow chemistry to achieve the effect of mild reaction conditions and fast reaction speed

Active Publication Date: 2021-01-19
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Previously, Meng and co-workers used a C-2′-modified cinchona base phase transfer catalyst to photocatalytically oxidize β-dicarbonyl compounds under batch conditions for asymmetric α-hydroxylation, but this reaction has not yet been demonstrated in a microreactor. conduct

Method used

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  • A method for the continuous preparation of chiral α-hydroxy-β-dicarbonyl compounds by visible light-catalyzed molecular oxygen oxidation via a microreactor
  • A method for the continuous preparation of chiral α-hydroxy-β-dicarbonyl compounds by visible light-catalyzed molecular oxygen oxidation via a microreactor
  • A method for the continuous preparation of chiral α-hydroxy-β-dicarbonyl compounds by visible light-catalyzed molecular oxygen oxidation via a microreactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] Take by weighing 0.05mmol 1-indanone-2-carboxylate adamantyl (Ia-1), 10% PTC-2, 1% tetraphenylporphyrin, put into 10ml test tube, add 5ml toluene, solid dissolves completely, and is recorded as A bottle; another 0.5% potassium carbonate solution is prepared, which is recorded as bottle b, at 0°C, the light source is white light, the organic phase in bottle a is pumped from pump A at a rate of 0.3ml / min, and the alkaline solution in bottle b is pumped from pump B at a rate of The flow rate of oxygen into C is 0.3ml / min, the flow rate of oxygen is 1ml / min, and the residence time is about 1.5min. The conversion rate of the reaction reaches 99.9%, the selectivity of α-hydroxylation product is more than 95%, and the ee value is 84%.

Embodiment 2

[0031]

[0032] Take by weighing 0.05mmol 1-indanone-2-carboxylate adamantyl (Ia-1), 10% PTC-2, 1% tetraphenylporphyrin, put into 10ml test tube, add 5ml toluene, solid dissolves completely, and is recorded as bottle a; another 0.5% potassium carbonate solution is prepared, which is recorded as bottle b, at 0°C, the light source is white light, the organic phase in bottle a is pumped from pump A at a rate of 1.5ml / min, and the alkaline solution in bottle b is pumped from pump B at a rate of The flow rate of oxygen into C is 1.5ml / min, the flow rate of oxygen is 2ml / min, and the residence time is about 1.5min. The conversion rate of the reaction reaches 99.9%, the selectivity of α-hydroxylation product is more than 95%, and the ee value is 80%.

Embodiment 3

[0034]

[0035] Take by weighing 0.05mmol 1-indanone-2-carboxylate adamantyl (Ia-1), 10% PTC-3, 1% tetraphenylporphyrin, put into 10ml test tube, add 5ml toluene, solid dissolves completely, and is recorded as bottle a; another 0.5% potassium carbonate solution is prepared, which is recorded as bottle b, at 0°C, the light source is white light, the organic phase in bottle a is pumped from pump A at a rate of 1.5ml / min, and the alkaline solution in bottle b is pumped from pump B at a rate of The flow rate of oxygen into C is 1.5ml / min, the flow rate of oxygen is 2ml / min, and the residence time is about 1.5min. The conversion rate of the reaction reaches 99.9%, the selectivity of α-hydroxylation product is more than 95%, and the ee value is 84%.

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Abstract

Belonging to the field of flow chemistry, the invention provides a method for continuous preparation of a chiral alpha-hydroxy-beta-dicarbonyl compound by visible light catalyzed molecular oxygen oxidation with a microreactor. The method utilizes a chiral quinine derivative quaternary ammonium salt as the chiral phase transfer catalyst, in the presence of an organic photosensitizer, by means of microreactor, preparation of the chiral alpha-hydroxy-beta-dicarbonyl compound by visible light activated gas molecular oxygen catalyzed continuous oxidation of a beta-dicarbonyl compound. The method provided by the invention can achieve a substrate conversion rate close to 100% in 1-10min reaction residence time, a product selectivity higher than 95%, and a product stereoselectivity ee value higherthan 80%. The reaction is green, the environmental burden is low, and the method realizes a continuous process, and has the advantages of large-scale production and low cost.

Description

technical field [0001] The invention belongs to the field of flow chemistry, and uses a microreactor to realize a method for preparing a chiral alpha-hydroxyl-beta-dicarbonyl compound by catalyzing and continuously oxidizing a beta-dicarbonyl compound with molecular oxygen activated by visible light. Background technique [0002] Currently, global flow chemistry is used in pharmaceutical, chemical, academic and research, petrochemical and other industries. Among flow chemical reactor types, microchannel reactions are the most widely used technology worldwide. Using a microchannel continuous flow reactor to prepare compounds has obvious advantages: 1) efficiency is improved, conversion rate and selectivity are also improved; 2) stability and safety can be well guaranteed; 3) green, low-carbon, sustainable continued. [0003] Previously, when Novartis was doing the nitration reaction of 8-bromo-1H-2-quinolinone (Org.Process Res.Dev.2011,15,1447~1452), it replaced the tank re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/31C07D211/16C07B41/02C07C69/757
CPCC07B41/02C07B2200/07C07C67/31C07D211/16C07C2602/08C07C2602/10C07C69/757
Inventor 孟庆伟冯世豪唐晓飞杨帆武玉峰赵静喃马存飞于宗义李根恽磊宋博
Owner DALIAN UNIV OF TECH
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