通过碱促进自由基反应合成磷酸化腙和重氮膦酸盐

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC
Qihao Jin, Yi-Jie Wang, Prof. Xinxin Wu, Prof. Jian-Ping Zou
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引用次数: 0

摘要

在此,我们报告了通过P中心自由基加成的醛衍生腙的区域选择性磷酸化,扩大了C─P键的形成,包括二烷基亚磷酸酯。优化研究确定醋酸锰为有效氧化剂,硝酸银为最佳催化剂,实现温和高效的自由基磷酸化。值得注意的是,4-甲基苯磺酰腙发生了意想不到的转变,提供重氮膦酸盐而不是膦化产物。这项研究为C─P键形成提供了一种实用和通用的方法,并为自由基介导的腙功能化提供了新的见解,在制药和材料科学中具有潜在的应用前景。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Phosphorylated Hydrazones and Diazophosphonate Synthesis Through Base-Promoted Radical Reactions

Phosphorylated Hydrazones and Diazophosphonate Synthesis Through Base-Promoted Radical Reactions

Phosphorylated Hydrazones and Diazophosphonate Synthesis Through Base-Promoted Radical Reactions

Phosphorylated Hydrazones and Diazophosphonate Synthesis Through Base-Promoted Radical Reactions

Herein, we report a regioselective phosphonylation of aldehyde-derived hydrazones via P-centered radical addition, expanding C─P bond formation to include dialkyl phosphites. Optimization studies established manganese acetate as an efficient oxidant and silver nitrate as the optimal catalyst, enabling mild and efficient radical phosphonylation. Notably, 4-methylbenzenesulfonylhydrazones underwent an unexpected transformation, affording diazo phosphonates instead of phosphonylated products. This study offers a practical and versatile method for C─P bond formation and provides new insights into radical-mediated hydrazone functionalization, with potential applications in pharmaceuticals and materials science.

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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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