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P-F Bond Formation

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An efficient electrophilic fluorination of secondary phosphine oxides with Selectfluor provides direct access to phosphoric fluorides in good yield under mild conditions. In addition, one-pot P-O bond construction is achieved in the presence of water or alcohols to provide phosphinic acids or phosphinates.
Q. Chen, J. Zeng, X. Yan, Y. Huang, C. Wen, X. Liu, K. Zhang, J. Org. Chem., 2016, 81, 10043-10048.


An efficient fluorination of P(O)-H and P(O)-OH compounds using sulfuryl fluoride as the fluorination reagent provides fluorophosphonates and phosphonofluoridates under mild conditions and without additional oxidants. The method avoids the use of expensive reagents for fluoridation.
G.-F. Zhang, L.-J. Han, C.-F. Guan, C.-R. Ding, J. Org. Chem., 2023, 88, 13142-13148.


A photocatalyzed oxidative-fluorination approach employing SF6 as a formal electrophilic fluorinating reagent an innovative pathway to forge P(O)-F bonds. Notably, sulfur hexafluoride plays a dual role as both the oxidant and the fluorinating reagent under mild conditions.
Y.-L. Huang, Q.-Q. Zhang, C.-Y. Wang, Y. Zhao, X.-S. Wang, Org. Lett., 2024, 26, 5776-5781.


A sulfone iminium fluoride (SIF) reagent promotes a deoxyfluorination of phosphinic acids in just 60 s with excellent yields and scope. The same P(V)-F products can also be synthesized from secondary phosphine oxides.
L. P. Miller, J. A. Vogel, S. Harel, J. M. Krussman, P. R. Melvin, Org. Lett., 2023, 25, 1834-1838.