三级硫胺胺的核性替代:硫酸盐的构造
Xiangshuai Du1, Guodan Lu1, Tao Zhang1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
Organic letters
|February 27, 2025
概括
这项研究引入了一种使用三化酸 (TCCA) 和三酸 (TfOH) 合成硫酸的新方法. 这种高效的过程激活了硫胺,以用酒精进行轻微的核替代,避免金属催化剂.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 三级硫胺是有机合成中的多功能前体.
- 将硫胺转化为硫酸盐的高效方法是有价值的.
研究的目的:
- 开发一种新的,温和和高效的方法来合成硫酸.
- 用随时可用的试剂激活三级硫胺,用于核替代.
主要方法:
- 使用三化酸 (TCCA) 和三酸 (TfOH) 激活三级硫胺.
- 在现场生成电友硫胺盐.
- 产生的盐与各种酒精的核替代.
主要成果:
- 在温和的反应条件下有效形成硫酸.
- 广泛的基板范围,容纳各种三级硫胺和醇.
- 在整个反应过程中观察到高功能组耐受性.
- 没有过渡金属催化剂,提供更绿色的合成替代品.
结论:
- TCCA和TfOH的联合作用为硫胺激活提供了一个有效的策略.
- 这种方法提供了一种实用且多用途的硫酸盐的途径,与现有协议相比具有显著的优势.
相关概念视频
Amines to Sulfonamides: The Hinsberg Test
3.2K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.2K
Preparation and Reactions of Sulfides
4.7K
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.
4.7K
Electrophilic Aromatic Substitution: Sulfonation of Benzene
5.7K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
5.7K
Acid Halides to Esters: Alcoholysis
2.7K
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:
2.7K
Preparation of Alcohols via Substitution Reactions
5.7K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
5.7K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
148
Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
148


