Synthesis of Structurally Complex Silicon Frameworks through the First Sila-Aldol Reaction

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Abstract

Herein, we report on the first sila-aldol reaction, which emphasizes the tight connection between silicon and carbon chemistry. This novel synthetic method provides straightforward access to 2-oxahexasilabicyclo[3.2.1]octan-8-ide, a structurally complex silicon framework, in quantitative yield. Its structure was confirmed by NMR spectroscopy and X-ray crystallography, and it displays a distinctive charge-transfer transition. The complete mechanism of this highly selective rearrangement cascade is outlined and supported by density functional theory (DFT) calculations, which highlight the thermodynamic driving force and the low activation barriers of this powerful silicon-carbon bond-forming strategy.

Original languageEnglish
Pages (from-to)8089-8093
Number of pages5
JournalAngewandte Chemie / International Edition
Volume56
Issue number28
DOIs
Publication statusPublished - 3 Jul 2017

Keywords

  • Journal Article

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