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DOI: https://doi.org/10.6023/cjo202405019

综述与进展

金属催化的非活化炔烃氢膦酰化反应的机理研究进展

  • 刘依雨 ,
  • 胡喻栋 ,
  • 张清伟
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  • 中国科学技术大学精准智能重点实验室,化学与材料科学学院 合肥 230026

收稿日期: 2024-05-15

  修回日期: 2024-08-09

  网络出版日期: 2024-09-10

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Metal-Catalyzed Hydrophosphinylation of Non-activated Alkynes: A Mechanistic Perspective

  • Yi-Yu Liu ,
  • Yudong Hu ,
  • Qing-Wei Zhang
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  • Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, 230026
Yi-Yu Liu (left) studies chemistry at the University of Science and Technology of China (2021.9 to present). She joined Qing-Wei Zhang's group in March 2023, focusing on asymmetric catalysis and mechanistic study. Yudong Hu (middle) studies chemistry at the University of Science and Technology of China (2021.9 to present). He joined Qing-Wei Zhang's group in November 2023, focusing on asymmetric catalysis and mechanistic study.Qing-Wei Zhang (right) graduated from Lanzhou University with a B.S. and PhD degree. He then worked as a postdoctoral researcher at Tsinghua University (2012.7-2015.1) and the University of California, Berkeley (2015.3-2018.3). In March 2018, he joined the University of Science and Technology of China as a principal investigator. His research interests are asymmetric catalysis and the development of novel chiral ligands. †These authors contributed equally to this work.

Received date: 2024-05-15

  Revised date: 2024-08-09

  Online published: 2024-09-10

Supported by

NSFC (No. 22071224)

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摘要

通过对烯烃和炔烃的氢膦酰化加成反应合成膦化合物的方法一直被广泛研究。本文主要总结了非活化炔类化合物的氢膦酰化反应的两种不同机理：氧化加成-迁移插入-还原消除机理,即Chalk-Harrod型机理,以及质子转移-还原消除机理。文中分别详细讨论了两种不同机理的具体步骤,并论述了一些支持这些步骤的实验和计算证据。此外,还列举了少量其他类型的机理以及密切相关的共轭烯烃的氢膦酰化反应机理。

关键词： 氢膦酰化反应; 机理研究; Chalk-Harrod机理; 质子转移; 配体配体氢转移

本文引用格式

刘依雨 , 胡喻栋 , 张清伟 . 金属催化的非活化炔烃氢膦酰化反应的机理研究进展[J]. 有机化学, 0 : 240910 . DOI: 10.6023/cjo202405019

Abstract

The synthesis of phosphine compounds through the addition reaction of H-[P(O)] species to olefins and alkynes has been extensively studied. This paper mainly summarizes two different mechanisms of the addition of H-[P(O)] species to non-activated alkyne. One is the oxidative addition-migration insertion-reductive elimination mechanism, namely the Chalk-Harrod type mechanism, and the other is the proton transfer-reductive elimination mechanism. This article elaborates on the specific steps of each mechanism and discusses experimental and computational evidence supporting these steps. Additionally, a few other types of mechanisms are briefly mentioned. The mechanism of H-[P(O)] reaction with relevant conjugated dienes was also involved when closely related.

Key words： H-P(O) addition; mechanistic study; Chalk-Harrod type mechanism; proton transfer; ligand to ligand hydrogen transfer

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