使用电化学三组分反应,使用元素硫的三组分反应合成硫
Gongbo Liu1, Shuoyu Xu1, Yangyang Yue1
1Cancer Hospital of Dalian University of Technology, School of Chemistry, School of Chemical Engineering, Dalian, 116024, P. R. China. wzsong@dlut.edu.cn.
Chemical communications (Cambridge, England)
|May 28, 2024
概括
这项研究介绍了一种使用元素硫的无金属,无氧化剂的电化学合成thioesters. 这种方法提供了一种高效和化学选择性的方法,用于产生有价值的硫化合物.
科学领域:
- 有机化学 有机化学
- 电化学 电化学 电化学
- 合成方法论 合成方法论
背景情况:
- 铁是有机合成和药物化学中的关键功能组.
- 现有的合成路线通常需要恶劣的条件,金属催化剂或氧化剂,限制其范围和可持续性.
- 开发高效的,无金属和无氧化剂的酸合成方法是非常可取的.
研究的目的:
- 开发一种新的电化学三组分反应,用于合成硫.
- 为了实现这种合成,使用元素硫作为硫源,避免金属催化剂和氧化剂.
- 研究反应机制并证明其效率和化学选择性.
主要方法:
- 电化学三组分反应,涉及元素硫,α-基托酸和二醇.
- 通过电化学设计促进的激进的颠覆策略.
- 机理学研究以阐明反应途径.
主要成果:
- 在无金属和无氧化剂条件下,成功合成了各种类铁.
- 展示了高原子经济和步骤经济.
- 通过元素硫有效地捕获乙基,以形成碳基乙基.
- 随后,二醇对碳基基进行捕获,从而产生具有高化学选择性的二醇.
结论:
- 开发的电化学方法提供了一个可持续和高效的途径,以 thioesters.
- 在这种新型合成策略中,元素硫作为有效的硫源.
- 反应机制涉及通过电化学激素聚变产生的激素中间体.
相关概念视频
02:33Preparation and Reactions of Thiols
6.1K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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02:26Preparation and Reactions of Sulfides
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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02:17Structure and Nomenclature of Thiols and Sulfides
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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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01:22Electrophilic Aromatic Substitution: Sulfonation of Benzene
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01:12Acid Halides to Esters: Alcoholysis
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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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01:08Esters to Alcohols: Grignard Reaction
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The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the case of formate esters, secondary alcohols are formed.
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
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