New organosilanes based on N-methylpyrrole – Synthesis, structure and characterization

•Synthesis of seven novel N-methylpyrrole-substituted organosilanes.•Single crystal X-ray structure analyses of five silanes.•Thermally stable silanes including N-methylpyrrol-2-ylsilane (RSiH3).•Silanes with low sensitivity towards moisture.

The organosilanes trimethoxy(N-methylpyrrol-2-yl)silane (1), dimethoxybis(N-methylpyrrol-2-yl)silane (2), methoxytris(N-methylpyrrol-2-yl)silane (3), and tetrakis(N-methylpyrrol-2-yl)silane (7) were synthesized by lithiation of N-methylpyrrole with n-BuLi/TMEDA and subsequent reaction of the appropriate metalated species with Si(OMe)4. N-Methylpyrrol-2-ylsilane (4), bis(N-methylpyrrol-2-yl)silane (5), and tris(N-methylpyrrol-2-yl)silane (6) were obtained by treatment of compound 1 with DIBAL-H (diisobutylaluminium hydride), and silanes 2 and 3 by reaction with LiAlH4. Compounds 1–7 were characterized by 1H, 13C, 29Si NMR, ATR-IR and Raman spectroscopy, EI and ESI mass spectrometry, elemental analysis and single crystal X-ray diffraction analysis (2, 3, and 5–7). The silicon–hydrogen bond lengths are 1.360(2), 1.320(18) Å (5) and 1.386(18) Å (6). All compounds are thermally stable in the solid state and do not decompose prior to evaporation. The silanes are stable at ambient conditions for several days (1 and 4) or even months (2, 3 and 5–7).

Graphical abstractLithiated N-methylpyrrole (R-Li) was reacted first with tetramethyl orthosilicate followed by chemical reduction with metal hydrides to give novel organosilanes of the type R4−xSiHx (x = 0–3).Figure optionsDownload full-size imageDownload as PowerPoint slide