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Main Title: Catalytic difunctionalization of unactivated alkenes with unreactive hexamethyldisilane through regeneration of silylium ions
Author(s): Wu, Qian
Roy, Avijit
Irran, Elisabeth
Qu, Zheng-Wang
Grimme, Stefan
Klare, Hendrik F. T.
Oestreich, Martin
Type: Article
Abstract: A metal‐free, intermolecular syn‐addition of hexamethyldisilane across simple alkenes is reported. The catalytic cycle is initiated and propagated by the transfer of a methyl group from the disilane to a silylium‐ion‐like intermediate, corresponding to the (re)generation of the silylium‐ion catalyst. The key feature of the reaction sequence is the cleavage of the Si−Si bond in a 1,3‐silyl shift from silicon to carbon. A central intermediate of the catalysis was structurally characterized by X‐ray diffraction, and the computed reaction mechanism is fully consistent with the experimental findings.
Subject(s): alkenes
density functional calculations
homogeneous catalysis
silylium ions
Si@Si activation
Issue Date: 23-Oct-2019
Date Available: 13-Feb-2020
Language Code: en
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Sponsor/Funder: TU Berlin, Open-Access-Mittel - 2019
Journal Title: Angewandte Chemie International Edition
Publisher: Wiley
Volume: 58
Issue: 48
Publisher DOI: 10.1002/anie.201911282
Page Start: 17307
Page End: 17311
EISSN: 1521-3773
ISSN: 1433-7851
TU Affiliation(s): Fak. 2 Mathematik und Naturwissenschaften » Inst. Chemie » FG Organische Chemie / Synthese und Katalyse
Appears in Collections:Technische Universität Berlin » Publications

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