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A β‐Diketiminate‐Stabilized Sila‐Acyl Chloride: Systematic Access to Base‐Stabilized Silicon Analogues of Classical Carbonyl Compounds
Author(s) -
Do Dinh Cao Huan,
Protchenko Andrey V.,
Ángeles Fuentes M.,
Hicks Jamie,
Kolychev Eugene L.,
Vasko Petra,
Aldridge Simon
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807543
Subject(s) - chemistry , lewis acids and bases , aldehyde , organic synthesis , nucleophilic substitution , acyl chloride , chloride , nucleophile , combinatorial chemistry , organic chemistry , catalysis
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.