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Preparation method of thioester compounds

A compound and thioester technology, applied in the fields of organic chemistry, chemical instruments and methods, organic chemistry, etc., can solve problems such as unpleasant smell and catalyst poisoning, and achieve strong designability, easy operation and good reaction applicability. Effect

Active Publication Date: 2021-01-19
ZHEJIANG SCI-TECH UNIV
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  • Description
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Problems solved by technology

Most of these reactions use mercaptan as a common sulfur source. The main limitation of its application is that it has an unpleasant smell and is easy to poison the catalyst.

Method used

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  • Preparation method of thioester compounds
  • Preparation method of thioester compounds
  • Preparation method of thioester compounds

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Embodiment Construction

[0035] The present invention will be further described below in conjunction with specific embodiments.

[0036] Add nickel trifluoromethanesulfonate, 4,4'-di-tert-butyl-2,2'-bipyridine, molybdenum carbonyl, potassium carbonate, zinc iodide, water , arylboronic acid (II), sulfonyl chloride (III) and organic solvent 2mL, mixed and stirred evenly, according to the reaction conditions in Table 2, the reaction was completed for 16 hours, filtered, silica gel sample mixing, and purified by column chromatography to obtain the corresponding thioester compound (I), the reaction process is shown in the following formula:

[0037]

[0038] The raw material addition of table 1 embodiment 1~15

[0039]

[0040] Table 2

[0041]

[0042] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, Et is ethyl, OMe is methoxy, t-Bu is tert-butyl, Bu is butyl , i-Pr is isopropyl, Cy is cyclohexyl, and NMP is N-methylpyrrolidone.

[00...

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Abstract

The invention discloses a preparation method of thioester compounds, wherein the method comprises the following steps: adding nickel trifluoromethanesulfonate, 4,4'-di-tert-butyl-2,2'-dipyridyl, carbonyl molybdenum, potassium carbonate, zinc iodide, water, arylboronic acid and sulfonyl chloride into an organic solvent, gathering, reacting at the temperature of 120 DEG C for 16 hours, and after thereaction is completed, carrying out after-treatment to obtain the thioester compound. The preparation method has the advantages of simple operation, cheap and easily available reaction starting raw materials, strong substrate designability, wide substrate functional group tolerance range, high reaction efficiency, and no need of additional oxidants and reducing agents by using sulfonyl chloride as a sulfur source. Various thioester compounds can be synthesized according to actual requirements, so that the practicability of the method is widened while the operation is convenient.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a thioester compound. Background technique [0002] Thioester compounds are a very important class of skeleton molecules, which exist in various natural products and drug molecules (Tetrahedron Lett. 1996, 37, 4305-4308). Its special structure enables thioester compounds to have significant physiological activity and are widely used in the fields of medicine and pesticides (J. Med. Chem. 2014, 57, 2832-2842). Thioester compounds are also of great significance in organic synthesis. As an air-stable and convenient acyl donor, they have been widely used in the synthesis of various aldehydes, ketones, esters and amides. In addition, thioester compounds have also been successfully applied to protein synthesis (Science 1994, 266, 776-779). [0003] [0004] The method of synthesizing thioester compounds in current literature reports is mainly to directly ob...

Claims

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Application Information

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IPC IPC(8): C07B45/00C07C327/26C07C327/28C07D333/38
CPCC07B45/00C07C327/26C07C327/28C07D333/38
Inventor 祁昕欣包志鹏姚歆桐吴小锋
Owner ZHEJIANG SCI-TECH UNIV
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