From cyclic diaryl λ ³ -bromanes/chloranes to polyfuntionalized biarylsilanes via aryne σ-bonds

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While biarylsilanes are intriguing compounds with emerging applications, their synthesis is far from trivial. Herein, we report an unprecedented strategy that allows access to these challenging compounds under metal-free and mild conditions with full atom economy using cyclic diaryl bromanes and chloranes as substrates. Coupling occurs between these hypervalent compounds and aminosilanes via aryne-intermediate generation and insertion into the N–Si σ-bonds of aminosilanes. The presence of halogen atoms in the final products warrants the further expansion of this transformative technology through various cyclisation reactions to furnish 5- and 6-membered benzo-fused silacycles. Photophysical studies of the newly generated compounds, as well as DFT calculations, complete this research.