A β-diketiminate-stabilized sila-acyl chloride: systematic access to base-stabilized silicon analogues of classical carbonyl compounds

Journal article

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.

Authors: Do, D; Protchenko, A; Ángeles Fuentes, M; Hicks, J; Kolychev, E

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Angewandte Chemie International Edition
• Volume: 57
• Issue: 42
• Pages: 13907-13911
• Publication date: 2018-09-21
• Acceptance date: 2018-08-31
• DOI: 10.1002/anie.201807543
• EISSN: 1521-3773
• ISSN: 1433-7851
• Pmid: 30168242
• Language: English
• Keywords: silicon; nucleophilic substitution; carbonyl compounds; ligand effects; structure elucidation