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N-substituted boronobenzylphosphonates were evaluated as substrates in Suzuki–Miyaura coupling catalyzed by tetrakis(triphenylphosphine)palladium(0) and complex of palladium acetate and (2-biphenyl)dicyclohexylphosphine. It was proven that they may be considered as useful substrates for the preparation of functionalized aminophosphonates.

Five analogues of a novel group of boron derivatives of aminophosphonic acids  N -benzylamino-(3- boronphenyl)- S -methylphosphonic acid ( m -Ph S ), N -benzyla- mino-(4-boronphenyl)- S -methylphosphonic acid ( p -Ph S ), N - benzylamino-(2-boronphenyl)- R -methylphosphonic acid ( o - Ph R ), N -benzylamino-(3-boronphenyl)- R -methylphosphonic acid ( m -Ph R ), and N -benzylamino-(4-boronphenyl)- R -meth- ylphosphonic acid ( p -Ph R )  were studied using Fourier transform infrared (FT IR), Fourier transform Raman (FT RS), and surface-enhanced Raman (SERS) spectroscopies. Analysis of obtained FT IR and FT RS spectra show that all investigated compounds in the solid state exist as dimeric species formed by an H-bonding interaction between − B(OH) 2 moieties of each monomer. In addition, comparison of the wavenumbers, intensities, and broadness of bands from the FT Raman and SERS spectra allowed information to be obtained regarding the adsorption geometry of the investigated compounds immobilized onto an electrochemically roughened silver substrate.

Two groups of new boronic acids containing aminophosphonate functions were synthesized and characterized by NMR spectroscopy and ESI-MS. Both groups of compounds were obtained by simple reactions of prepared in situ tris(trimethylsilyl) phosphite with a corresponding imine. The synthesized compounds may serve as a potential new class of building blocks, BNCT agents and supramolecular host molecules.