The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

Debotra Sarkar; Vitaly Nesterov; Tibor Szilvási; Philipp J Altmann; Shigeyoshi Inoue

doi:10.1002/chem.201805604

The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

Chemistry. 2019 Jan 24;25(5):1198-1202. doi: 10.1002/chem.201805604. Epub 2018 Dec 20.

Authors

Debotra Sarkar¹, Vitaly Nesterov¹, Tibor Szilvási², Philipp J Altmann¹, Shigeyoshi Inoue¹

Affiliations

¹ WACKER-Institute of Silicon Chemistry and, Catalysis Research Center, Technische Universität München, Lichtenbergstraße 4, 85748, Garching bei München, Germany.
² Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 1415 Engineering Drive, Madison, WI, 53706-1607, USA.

PMID: 30444958
DOI: 10.1002/chem.201805604

Abstract

The first donor-acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl₃ (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene-NHC complex [(NHC)₂ (Ar)Si]Cl with water in the presence of GaCl₃ . Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO₂ GaCl₂ ]₂ , free silaacetal ArSi(H)(OR)₂ , silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl₃ , and phosphasilene-NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.

Keywords: N-heterocyclic carbenes; silaaldehydes; silacarbonyl groups; silanones; silyliumylidenes.

Grants and funding

SILION 637394/H2020 European Research Council