在环境良好的条件下选择性铜催化原子转移激素添加 (ATRA) 在水中
Nutchanikan Phiromphu1, Methasit Juthathan1, Pattira Suktanarak2
1Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. pannee.l@chula.ac.th.
Dalton transactions (Cambridge, England : 2003)
|September 28, 2023
概括
绿色铜催化使得四化碳添加到水中的 styrene 使用新型催化剂. 这种简单,高效的方法在温和的条件下运行,为化学合成提供了一种可持续的方法.
科学领域:
- 绿色化学 绿色化学
- 催化剂是一种催化剂.
- 有机合成 有机合成
背景情况:
- 铜催化原子转移基添加 (ATRA) 反应在有机合成中至关重要.
- 传统的ATRA方法通常需要恶劣的条件或有机溶剂.
研究的目的:
- 为水中的铜催化ATRA反应开发简单的绿色条件.
- 研究一种用于选择性ATRA反应的新型铜催化剂.
主要方法:
- 使用一个铜复合物[Cu(ADPA) ((H2O) ((ClO4) 2),用L-亚斯科布酸作为还原剂.
- 使用生物相容表面活性剂 (Tween 20或Tween 80),以促进水性介质中的反应.
- 在温和温度 (60°C) 和环境大气下进行的反应.
主要成果:
- 使用开发的催化系统实现四化碳到烯的选择性ATRA.
- 证明了反应通过单电子转移 (SET) 机制进行.
- 获得了令人满意的优异基质转换和产品产量与各种基质.
结论:
- 开发了一种简单的绿色协议,用于水中的铜催化ATRA反应.
- 水性分散系统为传统的ATRA方法提供了一个可持续的替代方案.
- 该协议是高效的,需要较低的催化剂负荷 (1mol%),并且适用于各种基板.
相关概念视频
Radical Anti-Markovnikov Addition to Alkenes: Overview
3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Radical Formation: Addition
1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
3.8K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
3.8K
Preparation of Alcohols via Addition Reactions
6.3K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.3K
Radical Substitution: Allylic Chlorination
2.3K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.3K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
8.5K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
8.5K

![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
