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A method for rapid preparation of benzylselenide compounds based on selenium-directed carbon-hydrogen bond boronation

A technology for carbon-hydrogen bond boron and selenium compounds is applied in the field of rapid preparation of benzyl selenium compounds based on selenium-directed carbon-hydrogen bond boronation, and can solve the problem of great harm to the human body and the environment, few types of selenium-containing compounds, difficult to obtain raw materials and prices, etc. problem, to achieve good reproducibility

Active Publication Date: 2022-07-08
SOUTHWEST PETROLEUM UNIV
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AI Technical Summary

Problems solved by technology

However, there are relatively few existing chemical synthesis methods, and there are fewer types of selenium-containing compounds that can be synthesized, and these methods are more or less difficult to obtain raw materials and have high prices, no production benefits, or raw materials are highly toxic and harmful to the human body. A series of problems such as large environmental damage

Method used

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  • A method for rapid preparation of benzylselenide compounds based on selenium-directed carbon-hydrogen bond boronation
  • A method for rapid preparation of benzylselenide compounds based on selenium-directed carbon-hydrogen bond boronation
  • A method for rapid preparation of benzylselenide compounds based on selenium-directed carbon-hydrogen bond boronation

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of 2-(3-fluoro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane.

[0047] Weigh (1,5-cyclooctadiene) iridium (I) dichloride dimer (2.7 mg, 0.004 mmol) tricyclohexylphosphine (2.2 mg, 0.008 mmol) into a Shrek tube, under inert gas protection At 80 ° C for 20 min, add bis-boronic acid pinacol ester (25.4 mg, 0.1 mmol), add (2-fluorobenzyl) (phenyl) selenium (53.2 mg, 0.2 mmol) and pinacol borane (100 μL, 6.8 mmol) The reaction was stirred at 80° C. for 24 h. The resulting reactant was purified by silica gel column (petroleum ether / ethyl acetate) to give 2-(3-fluoro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl -1,3,2-Dioxaborane (62 mg) in 80% yield.

[0048] The structural formula of 2-(3-fluoro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane is as follows:

[0049]

[0050] NMR of the product 2-(3-fluoro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane Hydrogen and carbon NMR ...

Embodiment 2

[0052] Synthesis of 2-(3-chloro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane.

[0053] Weigh (1,5-cyclooctadiene) iridium (I) dichloride dimer (2.7 mg, 0.004 mmol) tricyclohexylphosphine (2.2 mg, 0.008 mmol) into a Shrek tube, under inert gas protection At 80° C. for 20 min, bis-boronic acid pinacol ester (25.4 mg, 0.1 mmol) was added, (2-chlorobenzyl) (phenyl) selenium (56.4 mg, 0.2 mmol) and pinacol borane were added. (100 μL, 6.8 mmol) The reaction was stirred at 80° C. for 24 h. The resulting reactant was purified by silica gel column (petroleum ether / ethyl acetate) to obtain 2-(3-chloro-2-(((phenylselenoyl)methyl)phenyl)-4,4,5,5-tetramethyl -1,3,2-dioxaborane (62 mg) in 76% yield.

[0054] The structural formula of 2-(3-chloro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane is as follows:

[0055]

[0056] Hydrogen NMR of 2-(3-Chloro-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane Spectrosco...

Embodiment 3

[0058] Synthesis of 2-(3-bromo-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane.

[0059] Weigh (1,5-cyclooctadiene) iridium (I) dichloride dimer (2.7 mg, 0.004 mmol) tricyclohexylphosphine (2.2 mg, 0.008 mmol) into a Shrek tube, under inert gas protection At 80° C. for 20 min, bis-boronic acid pinacol ester (25.4 mg, 0.1 mmol) was added, (2-bromobenzyl) (phenyl) selenium (65.2 mg, 0.2 mmol) and pinacol borane were added. (100 μL, 6.8 mmol) The reaction was stirred at 80° C. for 24 h. The resulting reactant was purified by silica gel column (petroleum ether / ethyl acetate) to give 2-(3-bromo-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl -1,3,2-dioxaborane (59 mg) in 66% yield.

[0060] The structural formula of 2-(3-bromo-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane is as follows:

[0061]

[0062] Hydrogen NMR of 2-(3-Bromo-2-(((phenylselenyl)methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborane Spectroscopy and C...

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Abstract

The invention provides a method for rapidly preparing benzyl selenium compounds based on selenium-directed carbon-hydrogen bond boronation, belonging to the field of organic synthesis. Under relatively mild conditions, the present invention uses selenium-containing organic compounds (benzyl phenyl selenium derivatives) as raw materials, cheap pinacol borane as the boron source, and double boron pinacol ester as the additive. The transition metal iridium is used as a catalyst to catalyze the reaction of carbon-hydrogen bond activation at the ortho position, thereby preparing a series of boronated products of organoselenium compounds. The advantages of the present invention are: the yield of the product is high, the reaction conditions are warm, and the organic selenium boride can be conveniently and quickly converted into a new organic selenium compound, and the spatial configuration is kept unchanged, and the good activity is maintained for the synthesis of organic selenium. new method. Therefore, the present invention provides an effective solution for the industrial production of other high-value compounds containing this structure in the future.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry including the preparation of pharmaceutical intermediates and related chemistry, in particular to a method for rapidly preparing benzyl selenoside compounds based on selenium-directed carbon-hydrogen bond boronation. Background technique [0002] Selenium-containing organoboron intermediates are a very useful class of intermediates in organic synthesis, which can be transformed into other compounds while keeping their steric configuration unchanged. Therefore, selenium-containing organoboron intermediates can be synthesized to expand the types of selenium compounds. Organic selenium compounds have a wide range of applications in medicine, health care, industry, etc., and also have potential application value in life science, information science and other fields. Guangzhou Chemical Industry, 2017, 45(22): 14-16. Wang Xiaomin. Production, consumption and application prospects of selenium ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 周太刚李兴圳唐佳刘林鹏
Owner SOUTHWEST PETROLEUM UNIV
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