在使用N-HN-异环碳素Pd复合体的Heck反应中进行协调加速催化
Alexis P Harper1, Alexandra J S Larson1, Lindsey M Brown1
1Brigham Young University, Department of Chemistry and Biochemistry, Provo, Utah 84602, United States.
单位替代的N-H N-异环碳化合物 (NHC) 复合物通过参与协调性酒精基质来改善赫克反应. 这导致了更高的转换和区域选择性,具有广泛的基质范围和协同反应的潜力.
科学领域:
- 有机金属化学 有机金属化学
- 催化剂是一种催化剂.
- 有机合成 有机合成
背景情况:
- 赫克反应是有机合成中的一个关键的碳-碳键形成反应.
- N-异环碳素 (NHC) 配体在增强过渡金属催化方面表现有前途.
- 在赫克反应中控制区域选择性和转换率仍然是积极研究的领域.
研究的目的:
- 为了研究在赫克反应中使用单替代的N-H NHC复合物.
- 探索协调酒精基质在提高赫克反应效率中的作用.
- 为了证明这种催化系统用于合成复杂有机分子的多功能性.
主要方法:
- 在催化赫克合反应中利用单替代的N-H NHC配体.
- 使用的基板具有协调性酒精组和不同的长.
- 研究了随后的氧化还原异构化和并联Heck合/氧化反应.
主要成果:
- 单替代的NHC复合物与协调性酒精基质接触,显著增加了赫克反应转换和区域选择性.
- 确定NHC连接体结构,基质协调组和长为催化改善的关键因素.
- 对于各种烯和烯来说,已经证明了广泛的基质范围,并通过双重反应成功合成了四基产物.
结论:
- 单替代的N-H NHC复合体为增强赫克反应提供了一个强大的策略.
- 开发的催化系统可以有效地获得有价值的化物,胺和四基衍生物.
- 这项工作扩大了NHC基催化在复杂有机合成中的实用性.
更多相关视频
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
12:19Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
相关概念视频
Catalysis
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)