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High-selectivity silane-based olefin and preparation method thereof

An alkyl olefin, high-selectivity technology, applied in chemical instruments and methods, silicon-organic compounds, organic chemistry, etc., can solve the problems of low regional and stereoselectivity, difficult conversion, etc., and achieve low regional and stereoselectivity. , to solve the transformation difficulties, the effect of mild reaction conditions

Active Publication Date: 2020-05-12
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the above-mentioned problems existing in the prior art, the present invention provides a highly selective silane-based olefin and a preparation method thereof, which uses iron to catalyze the selective silanization of non-activated aliphatic gem-difluoroalkenes, with mild reaction conditions and the preparation of Short and efficient process, high-efficiency synthesis of gem-disilyl olefins with controllable regio and stereoselectivity, and silylated fluoroolefins with controllable Z / E selectivity, effectively solving the problem of low regio and stereoselectivity and difficult conversion question

Method used

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  • High-selectivity silane-based olefin and preparation method thereof
  • High-selectivity silane-based olefin and preparation method thereof
  • High-selectivity silane-based olefin and preparation method thereof

Examples

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Effect test

Embodiment 1

[0033] A kind of preparation method of highly selective gem-disilazyl olefin comprises the following steps:

[0034](1) Weigh 0.02mmol iron triacetylacetonate, 0.04mmol 1,3-bis(diphenylphosphine)propane and 0.55mmol sodium tert-butoxide in a glove box and put them into a pressure-resistant sealed tube to obtain mixed raw materials, take out After connecting the double-row pipe, use nitrogen to pump and ventilate 3 times, each time at an interval of 4 minutes, and then replace the rubber plug and then use nitrogen to pump and ventilate 3 times, each time at an interval of 4 minutes;

[0035] (2) Add 0.2mmol (5,5-difluoropent-4-en-1-yl)benzene, 0.7mmol triethyl (4,4,5, 5-Tetramethyl-1,3,2-dioxaborolan-2-yl)silane and 1mL tetrahydrofuran were reacted at 70°C and 520rpm for 12h to obtain the reactant;

[0036] (3) Quench the reactant obtained in step (2) with a saturated solution of ammonium chloride, then extract 3 times with ethyl acetate, 30 mL each time, combine the organic p...

Embodiment 2

[0042] A preparation method of highly selective Z-fluorosilyl olefins, comprising the following steps:

[0043] (1) Take by weighing 0.02mmol ferrous iodide, 0.02mmol 1,3-bis(diphenylphosphine)butane and 0.9mmol sodium tert-butoxide in a glove box and put it into a pressure-resistant sealed tube to obtain the mixed raw materials, After taking it out, connect the double-row pipe with nitrogen pumping for 3 times, each interval of 4 minutes, and then replace the rubber plug and then use nitrogen pumping for 3 times, each interval of 4 minutes;

[0044] (2) Add 0.2mmol (4,4-difluorobut-3-en-1-yl)benzene, 0.5mmol triethyl (4,4,5, 5-Tetramethyl-1,3,2-dioxaborolan-2-yl)silane and 1mL tetrahydrofuran were reacted at -20°C and 450rpm for 12h to obtain the reactant;

[0045] (3) Quench the reactant obtained in step (2) with a saturated solution of ammonium chloride, then extract 3 times with ethyl acetate, 30 mL each time, combine the organic phases, dry over anhydrous sodium sulfate,...

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Abstract

The invention provides high-selectivity silane-based olefin and a preparation method thereof. The preparation method comprises the following steps that an iron catalyst, a ligand and sodium tert-butoxide are subjected to nitrogen extraction and gas exchange twice under the sealed condition, so that a mixed raw material is obtained; then, aliphatic gem-difluoroolefin, triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaboridine-2-yl)silane and an organic solvent are added to form a reactant; and after quenching, extraction, drying, filtration, vacuum concentration and purification are successively carriedout to obtain the high-selectivity silyl olefin. The invention also provides the high-selectivity silane-based olefin prepared by the method. According to the invention, iron catalysis is used for selective silanization of non-activated aliphatic gem-difluoroolefin, gem-disilyl olefin with controllable regioselectivity and stereoselectivity and silylated fluoroolefin with controllable Z / E selectivity are efficiently synthesized, and the problems of low regioselectivity and stereoselectivity and difficult conversion are effectively solved.

Description

technical field [0001] The invention belongs to the technical field of olefins and their preparation, and in particular relates to a highly selective silyl olefin and a preparation method thereof. Background technique [0002] Currently, the development of highly efficient and selective catalytic systems to obtain alkenes with controllable regio- and stereoselectivities is one of the most important research areas in organic chemistry. Silylated alkenes are important organic synthons, they have a wide range of transformations in organic chemistry, such as Pd-catalyzed cross-coupling reactions and Tamao-Fleming oxidation, etc., and possess desirable properties including easy handling, low cost and low toxicity and better stability relative to other vinyl metal species. Among them, gem-disilyl olefins are also important organic synthons, which can convert two silyl groups separately to obtain regioselective and stereoselective alkenes. [0003] In addition, organofluorine com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/0805C07F7/0827C07F7/081Y02P20/52
Inventor 冯璋张欢耿莎莎
Owner CHONGQING UNIV
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