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

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  • Dinh Cao Huan Do
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • Andrey V. Protchenko
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • M. Ángeles Fuentes
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • Jamie Hicks
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • Eugene L. Kolychev
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • Petra Vasko
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK
  • Simon Aldridge
    Department of Chemistry University of Oxford Inorganic Chemistry Laboratory South Parks Road Oxford OX1 3QR UK

書誌事項

公開日
2018-09-21
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/anie.201807543
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>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<jats:sup>IV</jats:sup> 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<jats:sup>II</jats:sup> 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.</jats:p>

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