阿尔基尼尔硫化物的光催化硫-反应
Oliver Bleton1, Noémie Beaucage1, Javier Guerrero-Morales1
1Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, Complexe des Sciences, 1375 Avenue Thérèse-Lavoie-Roux, Montréal H2 V 0B3, Québec, Canada.
The Journal of organic chemistry
|November 29, 2023
概括
这项研究引入了一种使用硫化和硫醇的新型醇-烯反应. 这种高效的方法,由光催化剂促进,为合成有价值的化学化合物提供了更好的反应性和区域选择性.
科学领域:
- 有机化学 有机化学
- 光催化作用的光催化
- 合成方法论 合成方法论
背景情况:
- 乙烯反应是多用途的碳-碳键形成反应.
- 传统的醇-烯反应使用醇和终端基因.
- 硫化硫化尚未被广泛地作为醇-烯反应中的基质进行探索.
研究的目的:
- 开发一种使用硫化酸的新型醇-烯反应.
- 为了研究这种新反应途径的效率和选择性.
- 为了比较基尼硫化物与传统基因在 thiol-yne 反应中的反应性.
主要方法:
- 使用了一种非金属光催化剂,eosin Y.
- 使用绿色发光二极管 (LED) 辐射.
- 在空气气氛下进行的反应.
主要成果:
- 在化硫酸与硫醇的转化中获得了良好的整体产量 (58-90%).
- 对于cis同位素有很高的选择性.
- 没有观察到对硫化的α位置的添加,表明受控的区域选择性.
- 与全碳内部基相比,表现出更好的反应性和区域选择性.
结论:
- 硫化酸是光催化硫酸反应的有效基质.
- 开发的方法提供了一个区域选择性和有效的途径,以功能化硫化物.
- 这种方法扩大了乙烯化学的范围,并提供了一种有价值的合成工具.
相关概念视频
Preparation and Reactions of Sulfides
4.8K
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.
4.8K
Preparation and Reactions of Thiols
6.2K
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.
6.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
7.7K
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.
7.7K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview
7.8K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
7.8K
Structure and Nomenclature of Thiols and Sulfides
4.8K
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,...
4.8K
Preparation of Alkynes: Alkylation Reaction
10.2K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.2K


![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)