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Method for cis-reduction of acetylenic bond in presence of iodo-vinyl

A technology of vinyl iodide and alkyne, applied in the field of organic chemistry, can solve problems such as unsatisfactory functional group compatibility

Inactive Publication Date: 2016-02-03
RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the functional group compatibility of iodovinyl compounds in organic synthesis is not ideal, and it will decompose under many reaction conditions (such as reduction of acetylenic bonds), which is also one of the main factors that limit the application of this important synthetic intermediate

Method used

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  • Method for cis-reduction of acetylenic bond in presence of iodo-vinyl

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Embodiment Construction

[0006]

[0007] Step 1: Take a 500mL flask, add 7g of nickel acetate tetrahydrate and 100mL of methanol, stir for 5 minutes, then add 1g of sodium borohydride in two batches, and react at room temperature for 1 hour.

[0008] Step 2: At room temperature, 1 mL of propylenediamine and 20 g of iodovinyl compound were sequentially added, and then stirred for 50 minutes under a hydrogen atmosphere of 1 atm.

[0009] Post-processing: evaporate to dryness under reduced pressure to remove methanol, dissolve the concentrate in 200mL ethyl acetate, wash with 100mL water, separate the organic phase, extract the water phase with 100mL ethyl acetate once, combine the organic phases obtained twice, The organic phase was dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure, separated with a silica gel column (petroleum ether / ethyl acetate 10 / 1), and concentrated to obtain 19 g of a colorless oil.

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Abstract

The invention provides a method for efficiently reducing an acetylenic bond into cis-double bones through P2-Ni hydrogenation in the presence of iodo-vinyl. As shown in general formula I, the method is concise in procedure, simple to operate, and high in yield and selectivity; iodo-vinyl and the acetylenic bond are very useful functional group synthons for organic synthesis, so that the method has higher applicability to organic synthesis.

Description

technical field [0001] The invention provides a method for efficiently reducing an alkyne bond to a cis double bond by utilizing P2-Ni hydrogenation in the presence of iodovinyl, belonging to the technical category of organic chemistry. Background technique [0002] Iodovinyl compound is a conjugated structure formed by iodine atom replacing a hydrogen atom on the carbon-carbon double bond. It is one of the best substrates for transition metal-catalyzed coupling reactions, and can be passed through Heck, Suzuki-Miyaura, Sonagashira and other common Pd-catalyzed coupling reactions to complete the assembly of carbon-carbon bonds. In addition, iodovinyl compounds can also be activated to form magnesium salts, lithium salt reagents or other organometallic reagents to undergo nucleophilic addition to carbonyl compounds. Therefore, iodovinyl compounds are very important in organic synthesis. synthon. [0003] However, the functional group compatibility of iodovinyl compounds in ...

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Application Information

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IPC IPC(8): C07C67/303C07C69/65
Inventor 张幸刘军杜宇国
Owner RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI