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Article

Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing

by
Vera V. Voinova
1,
Eugeniy S. Turyshev
2,
Sergey S. Novikov
1,3,
Nikita A. Selivanov
1,
Alexander Yu. Bykov
1,
Ilya N. Klyukin
1,
Andrey P. Zhdanov
1,*,
Mikhail S. Grigoriev
4,
Konstantin Yu. Zhizhin
1 and
Nikolay T. Kuznetsov
1
1
N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia
2
Institute for African Studies of the Russian Academy of Sciences (IAS), st. Spiridonovka 30/1, 123001 Moscow, Russia
3
Faculty of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, Russia
4
Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr. 31, Bldg 4, 119071 Moscow, Russia
*
Author to whom correspondence should be addressed.
Molecules 2026, 31(2), 231; https://doi.org/10.3390/molecules31020231
Submission received: 26 November 2025 / Revised: 19 December 2025 / Accepted: 7 January 2026 / Published: 9 January 2026
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Abstract

This work explores a novel and efficient synthetic approach to a new class of boron cluster derivatives via the nucleophilic addition of stabilized phosphorus ylides, Ph3P=CHR2 (R2 = COOEt, CN), to a series of nitrilium salts of the closo-decaborate anion, [2-B10H9NCR1]− (R1 = Me, Et, nPr, iPr, Ph). The reaction proceeds regio- and stereospecifically, affording a diverse range of iminoacyl phosphorane derivatives, [2-B10H9NH=C(R1)C(PPh3)R2]−, in high isolated yields (up to 95%). The obtained compounds (10 examples) were isolated as tetrabutylammonium or tetraphenylphosphonium salts and thoroughly characterized by multinuclear NMR (11B, 1H, 13C, 31P), high-resolution mass spectrometry, and single-crystal X-ray diffraction. The reaction feasibility was found to be strongly influenced by the steric hindrance of the R1 group. Furthermore, the practical utility of these novel hybrids was demonstrated by employing the [2-B10H9NH=C(CH3)C(COOC2H5)=PPh3]− anion as a highly effective membrane-active component in ion-selective electrodes. The developed tetraphenylphosphonium (TPP+) sensor exhibited a near-Nernstian response, a low detection limit of 3 × 10−8 M, and excellent selectivity over a range of common inorganic and organic cations, showcasing the potential of closo-borate-based ionophores in analytical chemistry.
Keywords: closo-decaborate; phosphorus ylides; nucleophilic addition; ion-selective electrodes closo-decaborate; phosphorus ylides; nucleophilic addition; ion-selective electrodes

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MDPI and ACS Style

Voinova, V.V.; Turyshev, E.S.; Novikov, S.S.; Selivanov, N.A.; Bykov, A.Y.; Klyukin, I.N.; Zhdanov, A.P.; Grigoriev, M.S.; Zhizhin, K.Y.; Kuznetsov, N.T. Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing. Molecules 2026, 31, 231. https://doi.org/10.3390/molecules31020231

AMA Style

Voinova VV, Turyshev ES, Novikov SS, Selivanov NA, Bykov AY, Klyukin IN, Zhdanov AP, Grigoriev MS, Zhizhin KY, Kuznetsov NT. Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing. Molecules. 2026; 31(2):231. https://doi.org/10.3390/molecules31020231

Chicago/Turabian Style

Voinova, Vera V., Eugeniy S. Turyshev, Sergey S. Novikov, Nikita A. Selivanov, Alexander Yu. Bykov, Ilya N. Klyukin, Andrey P. Zhdanov, Mikhail S. Grigoriev, Konstantin Yu. Zhizhin, and Nikolay T. Kuznetsov. 2026. "Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing" Molecules 31, no. 2: 231. https://doi.org/10.3390/molecules31020231

APA Style

Voinova, V. V., Turyshev, E. S., Novikov, S. S., Selivanov, N. A., Bykov, A. Y., Klyukin, I. N., Zhdanov, A. P., Grigoriev, M. S., Zhizhin, K. Y., & Kuznetsov, N. T. (2026). Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing. Molecules, 31(2), 231. https://doi.org/10.3390/molecules31020231

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