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Recent Progress in the Selective Functionalization of P(O)–OH Bonds

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Abstract

As we all know, organic phosphorus compounds have high application values in chemical industries. Compared with traditional compounds with P–X (X = Cl, Br, I) and P–H bonds, phosphorylation reagents containing P(O)–OH bonds are stable, environmentally friendly, and inexpensive. However, in recent years, there have been few studies on the selective functionalization of P(O)–OH bonds for the fabrication of P–C and P–Z bonds. In general, four-coordinated P(O)–OH compounds have reached coordination saturation due to the phosphorus atom center, but cannot evolve the phosphorus coordination center through intra-molecular tautomerization; however, the weak coordination effects between the P=O bond and transition metals can be utilized to activate P(O)–OH bonds. This review highlights the most important recent contributions toward the selective functionalization of P(O)–OH bonds via cyclization/cross coupling/esterification reactions using transition metals or small organic molecules as the catalyst.

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Acknowledgements

This work was supported by National Natural Science Foundation of China (21606080), Natural Science Foundation of Hunan Province (2019JJ50203), Scientific Research Fund of Hunan Provincial Education Department (19A197), Innovation research group project of Natural Science Foundation of Hunan Province (no. 2020JJ1004) and Hunan Provincial Innovation Foundation for Postgraduate (CX20201132). W.-Y.W. thanks the Hong Kong Polytechnic University (1-ZE1C) and the Endowed Professorship in Energy from Ms Clarea Au (847S) for the financial support. P.-C. Q. thanks the Foundation of Wenzhou Science & Technology Bureau (no. W20170003) and the National Natural Science Foundation of China (no. 21828102) for support.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414006, People’s Republic of China

    Biquan Xiong, Shipan Xu, Yu Liu & Ke-Wen Tang

  2. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, People’s Republic of China

    Biquan Xiong & Wai-Yeung Wong

  3. Key Laboratory of Environmental Functional Materials Technology and Application of Wenzhou City, Institute of New Materials and Industry Technology, College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, People’s Republic of China

    Peng-Cheng Qian

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  1. Biquan Xiong
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Correspondence to Biquan Xiong, Ke-Wen Tang, Peng-Cheng Qian or Wai-Yeung Wong.

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Xiong, B., Xu, S., Liu, Y. et al. Recent Progress in the Selective Functionalization of P(O)–OH Bonds. Top Curr Chem (Z) 379, 5 (2021). https://doi.org/10.1007/s41061-020-00319-1

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