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

doi:10.6023/cjo202405019

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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^*

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

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

Yi-Yu Liu^†, Yudong Hu^†, Qing-Wei Zhang^*

Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, 230026

Received:2024-05-15 Revised:2024-08-09
Contact: *E-mail: qingweiz@ustc.edu.cn
About author: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.
Supported by:
NSFC (No. 22071224)

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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Yi-Yu Liu, Yudong Hu, Qing-Wei Zhang. Metal-Catalyzed Hydrophosphinylation of Non-activated Alkynes: A Mechanistic Perspective[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjo202405019.

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金属催化的非活化炔烃氢膦酰化反应的机理研究进展

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

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