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A method for fluoroalkylation of alkenes or alkynes under acetone induction

A fluoroalkylation and acetone technology, applied in the field of organic synthesis, can solve the problems of expensive catalysts, poor functional group compatibility, etc., and achieve the effects of efficient synthesis, excellent functional group compatibility, and excellent reaction diversity

Active Publication Date: 2021-09-14
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention intends to provide a novel method for the fluoroalkylation of alkenes and alkynes to solve the problem of poor functional group compatibility or the need to use expensive catalysts in the synthesis of such compounds in the prior art

Method used

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  • A method for fluoroalkylation of alkenes or alkynes under acetone induction
  • A method for fluoroalkylation of alkenes or alkynes under acetone induction
  • A method for fluoroalkylation of alkenes or alkynes under acetone induction

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preparation example Construction

[0042] The product prepared by the preparation method of the present invention can be separated and purified by various methods, and the methods include: recrystallization, column chromatography and the like. The above purification methods are conventional methods in this field. For example, when performing recrystallization, a mixed solvent of polar solvent and non-polar solvent can be used, preferably ethyl acetate-petroleum ether, ethanol-petroleum ether and other mixed solvents. When using column chromatography, the developer used can be a single solvent or a mixed solvent, such as petroleum ether or a mixed solvent of ethyl acetate-petroleum ether, etc.

[0043] The above-mentioned features mentioned in the present invention, or the features mentioned in the embodiments can be combined arbitrarily. All the features disclosed in the specification of this case can be used in combination with any combination, and each feature disclosed in the specification can be replaced by...

Embodiment 1-5

[0047]

[0048] Into a 25mL reaction tube, add (0.30mmol) the following bases, 47.2mg (0.30mmol, 1 equivalent) of compound A-1, argon replacement three times, add 2mL of acetone (Acetone), inject 66μL (0.45mmol) of compound B -1. After stirring for 16 hours under blue light irradiation, compound C-1 was obtained with the following yield (fluorine spectrum yield). 1 H NMR (400MHz, CDCl 3 )δ5.01(br,1H),4.33(q,J=7.2Hz,2H),4.31-4.23(m,1H),3.58-3.35(m,2H),2.85-2.70(m,2H),1.43 (s,9H),1.35(t,J=7.2Hz,3H). 19 F NMR (376MHz, CDCl 3 )δ-109.7(dt, J=264.3Hz, 15.0Hz, 1F), -113.4(dt, J=264.3Hz, 16.5Hz, 1F).C-1 is a new compound.

[0049] Table 1

[0050]

Embodiment 6-7

[0052]

[0053] Into a 25mL reaction tube, add (0.60mmol) the following bases, 47.2mg (0.30mmol, 1 equivalent) of compound A-1, add 2mL of acetone (Acetone) after argon replacement three times, inject 66μL (0.45mmol) of compound B -1, after stirring for 16 hours under blue light irradiation, compound C-1 was obtained, and the yield was as follows (fluorine spectrum yield, isolated yield in brackets). 1 H NMR (400MHz, CDCl 3 )δ5.01(br,1H),4.33(q,J=7.2Hz,2H),4.31-4.23(m,1H),3.58-3.35(m,2H),2.85-2.70(m,2H),1.43 (s,9H),1.35(t,J=7.2Hz,3H). 19 F NMR (376MHz, CDCl 3 )δ-109.7(dt, J=264.3Hz, 15.0Hz, 1F), -113.4(dt, J=264.3Hz, 16.5Hz, 1F).C-1 is a new compound.

[0054] Table 2

[0055]

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Abstract

The application discloses a method for fluoroalkylation using acetone as a solvent and as an electron donor compound in the technical field of organic synthesis. Under the irradiation of visible light, innovatively select cheap green acetone as a solvent and electron donor compound to obtain various fluoroalkyl-substituted alkenes, alkanes and their derivatives in high yield. The method has a simple reaction system, excellent atom economy, excellent functional group compatibility, and high stereoselectivity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for fluoroalkylating alkenes or alkynes induced by acetone. Background technique [0002] Due to the special properties of fluorine, fluorine-containing organic compounds are widely used in life science, biomedicine, and material science. Therefore, the development of efficient and concise new methodology for the synthesis of fluorine-containing organic compounds is the current key research direction of organofluorine chemistry. [0003] Alkenes and alkynes are a class of common, cheap and very important compounds. The difluoroalkylation of alkenes is to obtain some important biopharmaceutical intermediates (ChemMedChem, 2009, 4(3), 329-334; PCT Int .Appl., 2015042397, 26Mar 2015), especially the 1,2-addition of alkenes and alkynes using ethyl iodide difluoroacetate (B-1), can directly obtain fluorine-containing amino acids and synthesize fluorine-containing ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/22C07C69/675C07C69/67C07C69/635C07C69/734C07C271/14C07C22/00C07C69/65C07C69/73C07C205/56C07C43/225C07C21/18C07C255/50C07C25/13C07C269/06C07C67/347C07C17/275C07C17/278C07C201/12C07C41/30C07C253/30
CPCC07C17/275C07C17/278C07C21/18C07C22/00C07C25/13C07C41/30C07C43/225C07C67/347C07C69/635C07C69/65C07C69/67C07C69/675C07C69/73C07C69/734C07C201/12C07C205/56C07C253/30C07C255/50C07C269/06C07C271/14C07C271/22C07C2601/14
Inventor 贺春阳毛婷赵亮李晓飞
Owner ZUNYI MEDICAL UNIVERSITY