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Medientyp:
E-Artikel
Titel:
Stereospecific and Chemoselective Copper‐Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates
Beteiligte:
Scharfbier, Jonas;
Gross, Benjamin M.;
Oestreich, Martin
Erschienen:
Wiley, 2020
Erschienen in:Angewandte Chemie International Edition
Sprache:
Englisch
DOI:
10.1002/anie.201912490
ISSN:
1433-7851;
1521-3773
Entstehung:
Anmerkungen:
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>A method for the synthesis of benzylsilanes starting from the corresponding ammonium triflates is reported. Silyl boronic esters are employed as silicon pronucleophiles, and the reaction is catalyzed by copper(I) salts. Enantioenriched benzylic ammonium salts react stereospecifically through an S<jats:sub>N</jats:sub>2‐type displacement of the ammonium group to afford α‐chiral silanes with inversion of the configuration. A cyclopropyl‐substituted substrate does not undergo ring opening, thus suggesting an ionic reaction mechanism with no benzyl radical intermediate.</jats:p>