3 years ago

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

Synthesis of Structurally Complex Silicon Frameworks through the First Sila-Aldol Reaction
Ana Torvisco, Michaela Flock, Mario Leypold, Lukas Schuh, Roland Fischer, Michael Haas, Harald Stueger
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. Silicon, not carbon: The first sila-aldol reaction is reported. This transformation emphasizes the tight connection between silicon and carbon chemistry and enables the synthesis of a previously undescribed 2-oxahexasilabicyclo[3.2.1]octan-8-ide through an ensuing highly selective rearrangement cascade.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701862

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