REVIEW

Advances in Mechanistic Studies of Metal-Catalyzed Hydrophosphinylation of Non-Activated Alkynes

  • Yi-Yu Liu ,
  • Yudong Hu ,
  • Qing-Wei Zhang
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  • Key Laboratory of Precision and Intelligent Chemistry, School of Chemistry and Material Science, University of Science and Technology of China, Hefei 230026
†These authors contributed equally to this work.
*Corresponding authors. E-mail:

Received date: 2024-05-15

  Revised date: 2024-08-09

  Online published: 2024-09-10

Supported by

National Natural Science Foundation of China(22071224)

Abstract

The synthesis of phosphine compounds through the addition reaction of H-[P(O)] species to olefins and alkynes has been extensively studied. Two different mechanisms of the addition of H-[P(O)] species to non-activated alkyne are mainly summarized. 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 review 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.

Cite this article

Yi-Yu Liu , Yudong Hu , Qing-Wei Zhang . Advances in Mechanistic Studies of Metal-Catalyzed Hydrophosphinylation of Non-Activated Alkynes[J]. Chinese Journal of Organic Chemistry, 2024 , 44(12) : 3678 -3685 . DOI: 10.6023/cjoc202405019

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