用铜催化二甲基试剂的电友性氨化
Ashley M Berman1, Jeffrey S Johnson
1Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Journal of the American Chemical Society
|May 6, 2004
概括
本研究介绍了一种用铜催化方法,使用二甲基试剂和基胺衍生物制造三级胺. 方便的反应条件和高产量使其成为有机合成的宝贵工具.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- 三级氨基是制药和材料科学中至关重要的构建模块.
- 对于三级氨基的高效合成途径是非常受欢迎的.
- 现有的方法可能涉及恶劣的条件或复杂的程序.
研究的目的:
- 开发一种新,高效,方便的合成三级胺的方法.
- 为了利用铜催化剂对二甲试剂的电友氨化.
- 使用O-acyl N,N-dialkyl氧胺衍生物作为有效的氨基化剂.
主要方法:
- 在二甲基试剂和O-acyl N,N-dialkyl 氧胺衍生物之间发生铜催化反应.
- 优化反应条件,包括催化剂加载和溶剂选择.
- 由此产生的三级胺产品的净化和表征.
主要成果:
- 在高产量中成功合成各种三级胺.
- 用不同的二甲基试剂和xylamine衍生物证明反应的普遍性.
- 反应在温和条件下 (室温) 进行,并且是快速的 (1小时).
结论:
- 描述的铜催化氨化提供了一种通用和有效的通往三级胺的途径.
- 由于反应条件温和,通过酸提取直接隔离产品,该方法很方便.
- 这种方法为合成有价值的三级氨基化合物提供了切实可行的替代方案.
相关概念视频
Standard Electrode Potentials
On comparing the reactivity of silver and lead, it is observed that the two ionic species, Ag+ (aq) and Pb2+ (aq), show a difference in their redox reactivity towards copper: the silver ion undergoes spontaneous reduction, while the lead ion does not. This relative redox activity can be easily quantified in electrochemical cells by a property called cell potential. This property is commonly known as cell voltage in electrochemistry, and it is a measure of the energy which accompanies the charge...
Properties of Organometallic Compounds
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
Reactivity of Enolate Ions
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate base is localized on the oxygen...
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...


