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Selective Si−C(sp3 ) Bond Cleavage in (Aminomethyl)silanes by Carbanionic Nucleophiles and Its Stereochemical Course

Koller, Stephan G., Bauer, Jonathan O. and Strohmann, Carsten (2017) Selective Si−C(sp3 ) Bond Cleavage in (Aminomethyl)silanes by Carbanionic Nucleophiles and Its Stereochemical Course. Angewandte Chemie International Edition 56 (27), pp. 7991-7994.

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Other URL: http://doi.org/10.1002/anie.201702410


Abstract

Selective cleavage of a silicon-carbon bond in tetraorganosilanes is still a great challenge. A new type of Si-C(sp(3)) bond cleavage in bench-stable (aminomethyl)silanes with common organolithium reagents as nucleophiles has now been identified. Suitable leaving groups are benzyl, allyl, and phenylthiomethyl groups. A beta-donor function and polar solvents are essential for the reaction. Simple ...

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Item type:Article
Date:2017
Institutions:Chemistry and Pharmacy > Institut für Anorganische Chemie
Identification Number:
ValueType
10.1002/anie.201702410DOI
Keywords:CARBON-SILICON BOND; CROSS-COUPLING REACTIONS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOGENIC SILANES; CENTERED CHIRALITY; CRYSTAL-STRUCTURES; SI BOND; ARYL; REAGENTS; alkyllithium compounds; chirality; density functional calculations; nucleophilic substitution; silanes
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Item ID:38875
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