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A β-Diketiminate-Stabilized Sila-Acyl Chloride: Systematic Access to Base-Stabilized Silicon Analogues of Classical Carbonyl Compounds.

Dinh Cao Huan DoAndrey V ProtchenkoM Ángeles FuentesJamie HicksEugene L KolychevPetra VaskoSimon Aldridge
Published in: Angewandte Chemie (International ed. in English) (2018)
An oxidation/substitution strategy for the synthesis of silicon analogues of classical organic carbonyl compounds is reported, by making use of a novel β-diketiminate-supported sila-acyl chloride-the first example of such a compound isolated without the use of a stabilizing Lewis acid. Nucleophilic substitution at the SiIV center allows direct access to the corresponding sila-aldehyde and sila-ester. An alternative approach utilizing the reverse order of synthetic steps is thwarted by the facile rearrangement of the corresponding SiII systems featuring either H or OR substituents. As such, the isolation of (N-nacnac)Si(O)Cl represents a key step forward in enabling the synthesis of sila-carbonyl compounds by a synthetic approach ubiquitous in organic chemistry.
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