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Experimental and Computational Exploration of para‐Selective Silylation with a Hydrogen‐Bonded Template
Ist Teil von
Angewandte Chemie (International ed.), 2017-11, Vol.56 (47), p.14903-14907
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2017
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
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.