Please use this identifier to cite or link to this item: http://dx.doi.org/10.14279/depositonce-9657
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Main Title: Lewis acid catalyzed transfer hydromethallylation for the construction of quaternary carbon centers
Author(s): Walker, Johannes C. L.
Oestreich, Martin
Type: Article
Language Code: en
Abstract: The design and gram‐scale synthesis of a cyclohexa‐1,4‐diene‐based surrogate of isobutene gas is reported. Using the highly electron‐deficient Lewis acid B(C6F5)3, application of this surrogate in the hydromethallylation of electron‐rich styrene derivatives provided sterically congested quaternary carbon centers. The reaction proceeds by C(sp3)−C(sp3) bond formation at a tertiary carbenium ion that is generated by alkene protonation. The possibility of two concurrent mechanisms is proposed on the basis of mechanistic experiments using a deuterated surrogate.
URI: https://depositonce.tu-berlin.de/handle/11303/10762
http://dx.doi.org/10.14279/depositonce-9657
Issue Date: 12-Sep-2019
Date Available: 13-Feb-2020
DDC Class: 540 Chemie und zugeordnete Wissenschaften
Subject(s): boron
carbocations
C–C bond formation
Lewis acids
transfer processes
Sponsor/Funder: TU Berlin, Open-Access-Mittel - 2019
License: https://creativecommons.org/licenses/by-nc/4.0/
Journal Title: Angewandte Chemie International Edition
Publisher: Wiley
Publisher Place: Weinheim
Volume: 58
Issue: 43
Publisher DOI: 10.1002/anie.201909852
Page Start: 15386
Page End: 15389
EISSN: 1521-3773
ISSN: 1433-7851
Appears in Collections:FG Organische Chemie / Synthese und Katalyse » Publications

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