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Main Title: Stereospecific and chemoselective copper-catalyzed deaminative silylation of benzylic ammonium triflates
Author(s): Scharfbier, Jonas
Gross, Benjamin M.
Oestreich, Martin
Type: Article
Language Code: en
Abstract: 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 SN2‐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.
Issue Date: 4-Dec-2019
Date Available: 13-Feb-2020
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Subject(s): copper
nucleophilic substitution
Sponsor/Funder: DFG, 388910461, Ionische und radikalische Kreuzkupplungen zur Kohlenstoff‒Silicium-Bindungsknüpfung
TU Berlin, Open-Access-Mittel - 2019
Journal Title: Angewandte Chemie International Edition
Publisher: Wiley
Publisher Place: Weinheim
Volume: 59
Issue: 4
Publisher DOI: 10.1002/anie.201912490
Page Start: 1577
Page End: 1580
EISSN: 1521-3773
ISSN: 1433-7851
Appears in Collections:FG Organische Chemie / Synthese und Katalyse » Publications

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