n-Bu4NI/K2S2O8-介导的C-N合在化物和胺之间
Xiaochen Liu1,2, Samual Hee1,2, Netanel G Sapir1
1Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Queens, New York, 11367, United States.
European journal of organic chemistry
|July 25, 2024
概括
使用n-Bu4NI/K2S2O8的新型C-N合方法使得在电子效应的影响下,化物和胺的转化或交叉脱联合成为可能. 这种反应还促进了氧化循环形成quinazolin-4(3H) -ones.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 在有机合成中,C-N合反应是基本的.
- 开发有效和有选择的C-N债券形成方法仍然是一个关键的挑战.
研究的目的:
- 报告一种新型的n-丁酸 (n-Bu4NI) 和硫酸盐 (K2S2O8) 介导的C-N合反应.
- 为了研究电子效应对这种合中的芳香性化物基质的影响.
- 探索这种方法在合成quinazolin-4(3H) -ones中的应用.
主要方法:
- 使用n-丁酸 (n-Bu4NI) 和硫酸盐 (K2S2O8) 作为催化和氧化系统.
- 使用化物和化物作为C-N合的基质.
- 进行密度函数理论 (DFT) 计算以阐明反应机制.
- 对拟议的机制和反应结果进行实验验证.
主要成果:
- 从化物转化为胺的选择性转化,当芳香化物具有正极或电子捐赠群时.
- 在没有这样的电子捐赠群体的情况下,观察到交叉脱联的优势.
- 提供了单个电子转移机制的证据,其中涉及一个基中间体.
- 通过氧化循环化成功合成了四种quinazolin-4(3H) -one衍生物,产量为65-99%.
结论:
- 开发的n-Bu4NI/K2S2O8系统提供了基于基板电子的可调节选择性的C-N合的多功能方法.
- 反应通过单个电子转移机制进行,由DFT计算和实验数据证实.
- 这种方法提供了一条有效的通道到有价值的quinazolin-4(3H) -one支架.
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