铜介导的N-亚里尔-胺酸的合成
Margaux Badufle1, Frédéric Robert1, Yannick Landais1
1CNRS, Bordeaux INP, ISM, UMR 5255, University of Bordeaux, F-33400, Talence, France.
一种新的方法有效地利用铜催化交叉合合成N-aryloxamates和氧胺酸. 随后的转化为尿是通过热或可见光催化剂实现的,根据电子性质的不同效率.
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:
- 铜催化交叉合反应在有机合成中至关重要.
- 氧胺和氧胺酸是重要的合成中间体.
- 为N-arylation和随后的功能化开发高效的方法至关重要.
研究的目的:
- 通过乌尔曼-戈尔德伯格交叉合开发一种强大的合成N-aryloxamates的方法.
- 从N-aryloxamates中产生氧化酸的简单途径.
- 通过使用不同的催化系统,探索从氧化酸中合成尿的合成.
主要方法:
- 催化Ullmann-Goldberg交叉合的酸与含有大量三级基团的氧酸盐.
- N-aryloxamates的酸性水解以产生氧胺酸.
- 在热条件下或可见光Fe-LMCT (基于铁的光到金属的电荷转移) 过程中,使用PIDA (利胺(III) 乙酸盐) 将氧化酸转化为尿.
主要成果:
- N-aryloxamates在中等到优秀的产量中被合成,有庞大的基团防止降解.
- 氧胺酸通过酸水解获得了高产量的氧胺酸.
- 尿从缺乏电子的N-氧化酸中有效合成,但由于过度氧化,富含电子的对应物产量减少.
结论:
- 开发的Cu催化交叉合提供了一条可靠的途径到N-aryloxamates和oxamic酸.
- 热和可见光催化方法都可以用于从氧化酸合成尿.
- N-基组的电子性质显著影响了尿形成的效率,特别是在PIDA.
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