通过Pd/S,O-Ligand催化,通过非定向的C-H化化化衍生物
Ke-Zuan Deng1, Verena Sukowski1, M Ángeles Fernández-Ibáñez1
1van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands.
Angewandte Chemie (International ed. in English)
|February 24, 2024
概括
这项研究提出了一种新的非定向的C-H化方法,使用异离子衍生物作为限制试剂. 这种有效的二化合物合成避免了预功能化和指导组,提供了更简单的方法.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 非定向的C-H arylation提供了一条有效的途径,使二化合物.
- 作为限制反应物的简单的直接C-H化具有挑战性.
研究的目的:
- 开发一种新型的非定向C-H化异离子衍生物作为限制试剂.
- 在温和的条件下,在没有预功能化的情况下,实现直接的化.
主要方法:
- 使用无离子衍生物作为限制性试剂在直接的C-H与酸的 arylation.
- 采用了一步合成的S,O-配体来促进反应.
主要成果:
- 在温和条件下实现非定向的C-H化.
- 在合成有用的产量中获得的制产品.
- 证明了生物活性分子的成功结合.
结论:
- 开发的方法提供了一种高效和直接的合成双化合物的途径.
- 使用一种新型的S,O-连接体是这种C-H结合策略成功的关键.
相关概念视频
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
6.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.0K
01:10α-Alkylation of Ketones via Enolate Ions
3.1K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.1K
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.3K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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...
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...
3.3K
01:28Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.2K
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.
10.2K
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K