通过生物启发的C-S σ-键转化合成硫化物
Hongmei Liu1, Yuzhu Zheng1, Ke-Lin Xian1
1Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, 430074, China.
Chemistry (Weinheim an der Bergstrasse, Germany)
|February 25, 2025
概括
这项研究引入了一种新的生物启发的σ-键转化反应,模仿S-adenosylmethionine (SAM) 循环. 该方法有效地将有机硫化物和酒精转化为有价值的化合物,提供新的合成途径.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 生物有机化学 生物有机化学
背景情况:
- S-adenosylmethionine (SAM) 循环是一个至关重要的生物途径.
- 传统的C-X键形成反应在范围和效率上都有局限性.
- 开发用于C-X债券功能化的新催化方法是必不可少的.
研究的目的:
- 开发一种由自然SAM循环启发的新型混合s-键转化反应.
- 为了允许在有机硫化物中直接编辑 (sp3) 杂交的C-S键.
- 扩大 σ 键转解的范围,包括用于异环合成的 C-O 和 C-N 键.
主要方法:
- 在有机硫化物和酒精之间设计了一种混合的σ-键转化反应.
- 这种反应是由化 (AlCl3) 和化 (ZnI2) 的简易混合催化.
- 机械实验和DFT计算被用来阐明反应路径.
主要成果:
- 开发的方法允许在有机硫化物中直接功能化 (sp3) 杂交的C-S键.
- 反应提供了快速获取各种具有挑战性的有机硫化物.
- 该方法已成功扩展到分子内C-O和C-N键转基因,产生和的异环环,如循环乙烯,乙烯和氨基.
结论:
- 生物启发的C-S/C-O转化反应在合成有机化学中提供了一个强大的新工具.
- 这种方法为 σ 键转化提供了重要的洞察力,与自然 SAM 循环进行了平行.
- 该方法为在合成有价值的有机分子和异环环中取得进一步进展开辟了道路.
相关概念视频
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
Preparation and Reactions of Thiols
5.9K
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.
5.9K
Structure and Nomenclature of Thiols and Sulfides
4.5K
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,...
4.5K
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
The Sulfur Cycle
43.6K
Sulfur, an important element in the chemical makeup of proteins, is recycled through the atmosphere and aquatic and terrestrial environments. Found in the atmosphere as sulfur dioxide (SO2), sulfur is released by decaying organisms, weathered rocks, geothermal vents, volcanos, and burning fossil fuels. It is deposited into the ecosystem, cycled through the biotic community, and either released back into the atmosphere as gas or deposited in marine sediment for long-term storage and eventual...
43.6K
Thermal Sigmatropic Reactions: Overview
2.0K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.0K


