通过电子捐赠体接受体复合光激活和基添加到硫胺反应剂的选择性CH硫化
Joshua T Baxter1, Adrian Hall2, Michael C Willis1
1Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.
Organic letters
|October 14, 2025
概括
这项研究引入了一种新方法来制造硫胺,这是医学中重要的构建材料. 该过程使用蓝光和随时可用的化学物质进行高效的合成,避免昂贵的催化剂.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 合成化学 合成化学
背景情况:
- 亚利硫胺是合成诸如硫胺等具有医学意义的S(VI) 化合物的关键中间体.
- 目前用于合成硫胺的现有方法可能范围有限或需要昂贵的催化剂.
研究的目的:
- 开发一种新的,选择性地址的C-H硫化过程,用于酸硫胺.
- 建立一个操作简单和广泛适用的方法,用于后期的功能化.
主要方法:
- 采用了一种启用硫的,蓝光促进的电子捐赠者-接受器 (EDA) 复合体.
- 从光活性EDA复合物中使用单电子转移 (SET) 来产生基.
- 在温和条件下与硫胺试剂反应的基.
主要成果:
- 成功合成了具有广泛通用性的关键亚利硫胺物种.
- 证明了医学相关领域的选择性C-H硫化.
- 在不依赖昂贵的过渡金属或光电还原催化剂的情况下实现了合成.
结论:
- 开发的方法提供了一种高效和多用途的途径,可以获得硫胺.
- 这种方法是药物和药物发现化学中后期功能化的一个有价值的工具.
- 该过程的简单性和避免昂贵的催化剂提高了其实际效用.
更多相关视频
相关概念视频
Amines to Sulfonamides: The Hinsberg Test
4.4K
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 sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.4K
Preparation and Reactions of Sulfides
5.7K
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.
5.7K
Radical Reactivity: Nucleophilic Radicals
2.6K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.6K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
3.7K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.7K
Acid Halides to Esters: Alcoholysis
3.9K
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:
3.9K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
4.6K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.6K


