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

Abstract

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 Si^IV 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 Si^II 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.

Keywords: carbonyl compounds; ligand effects; nucleophilic substitution; silicon; structure elucidation.