3 years ago

Experimental and Computational Exploration of para-Selective Silylation with a Hydrogen-Bonded Template

Experimental and Computational Exploration of para-Selective Silylation with a Hydrogen-Bonded Template
Amit Dahiya, Srimanta Guin, Peng Liu, Sheng Feng, Arun Maji, Debabrata Maiti, Vikas Kumar Singh
The regioselective conversion of C−H bonds into C−Si bonds is extremely important owing to the natural abundance and non-toxicity of silicon. Classical silylation reactions often suffer from poor functional group compatibility, low atom economy, and insufficient regioselectivity. Herein, we disclose a template-assisted method for the regioselective para silylation of toluene derivatives. A new template was designed, and the origin of selectivity was analyzed experimentally and computationally. An interesting substrate–solvent hydrogen-bonding interaction was observed. Kinetic, spectroscopic, and computational studies shed light on the reaction mechanism. The synthetic significance of this strategy was highlighted by the generation of a precursor of a potential lipophilic bioisostere of γ-aminobutyric acid (GABA), various late-stage diversifications, and by mimicking enzymatic transformations. A template-assisted method for the regioselective para silylation of toluene derivatives is described. The origin of selectivity was analyzed both experimentally and computationally, and an interesting substrate–solvent hydrogen-bonding interaction was observed.

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

DOI: 10.1002/anie.201708449

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