光敏感的阿尔基因的Imino-Thiocyanation的形成
Cong Huang1, Zhen-Zhen Xie1, Jie Gao1
1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Organic letters
|February 17, 2025
概括
一种新的无金属方法使得olefins的光敏化1,2-imino-thiocyanation成为可能. 这种高效的反应从多种不同的原料中产生有价值的β-氨基基酸盐.
科学领域:
- 有机化学 有机化学
- 摄影化学的使用.
- 合成方法论 合成方法论
背景情况:
- 金属催化反应很普遍,但引发了环境和成本方面的担忧.
- 开发无金属合成路径对于可持续化学至关重要.
- 硫化反应对于引入硫和的功能非常重要.
研究的目的:
- 为了建立一个无金属的协议,对olefins的光敏化1,2-imino-thiocyanation.
- 为了利用一个易于获得的双功能试剂进行这种转化.
- 为合成含有β-氨基基酸盐的化合物提供一种新策略.
主要方法:
- 光敏感反应条件. 光敏感反应条件.
- 使用S-cyano-N-(diphenylmethylene) thiohydroxylamine作为一个双功能试剂.
- 优化与各种olefins的反应.
主要成果:
- 从广泛的烯酸中成功合成β-氨基酸盐.
- 对所需产品实现中等至高产量.
- 一个无金属,高效和原子经济的过程的演示.
结论:
- 开发的协议为烯功能化提供了一种有效的无金属策略.
- 反应表现出广泛的基质范围和高阶经济性.
- 这种方法可以访问重要的β-氨基酸酸支架.
相关概念视频
Cycloaddition Reactions: MO Requirements for Photochemical Activation
2.0K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.0K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
9.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.8K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
1.8K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.8K
Photochemical Electrocyclic Reactions: Stereochemistry
1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
1.8K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
7.6K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.6K
Oxidative Cleavage of Alkenes: Ozonolysis
9.9K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
9.9K


![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)