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

doi:10.6023/cjoc202405019

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3678-3685.DOI: 10.6023/cjoc202405019 Previous Articles Next Articles

REVIEW

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^*()

中国科学技术大学化学与材料科学学院精准智能化学重点实验室合肥 230026

收稿日期:2024-05-15 修回日期:2024-08-09 发布日期:2024-09-10
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(22071224)

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

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

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

Received:2024-05-15 Revised:2024-08-09 Published:2024-09-10
Contact: *E-mail:qingweiz@ustc.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22071224)

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.

Key words: hydrophosphorylation, 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. Advances in Mechanistic Studies of Metal-Catalyzed Hydrophosphinylation of Non-Activated Alkynes[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3678-3685.

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Fig. & Tab. 10

Scheme 1. Two possible pathways of H-P(O) addition

Scheme 2. Oxidative addition of H-P(O) to several transition metal atoms

Scheme 3. Hydrophospinylation of alkynes enabled by Sadphos ligand

Scheme 4. (a) Selected M-C intermediates in hydrophospinylation reactions; (b) possible mechanism of the formation of double alkyne addition product; (c) plural deuterium substituted products detected in the deuterium-labeling experiment

Scheme 5. (a) Activity of reduction elimination of different intermediate; (b) cross-over study of hydrophosphinylation of conjugated dienes

Scheme 6. Palladium-catalyzed H-P(O) addition reaction

Scheme 7. Mechanism of nickel-catalyzed hydrophosphinylation reaction of conjugated enynes

Scheme 8. Deuterium-labeling experiments in nickel-catalyzed system

Scheme 9. Results of DFT calculations of acid-free and acid-co-catalyzed H-P(O) addition to alkynes process

Scheme 10. Other mechanisms: (a) copper-catalyzed addition reaction; (b) mechanism of copper-catalyzed addition reaction

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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

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

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