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ISBN 9783843909334

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978-3-8439-0933-4, Reihe Organische Chemie

Sabine Grupe
The Iron App: Reductive Iron-Catalyzed C-H and C-C Bond Formations

155 Seiten, Dissertation Universität Regensburg (2013), Softcover, A5

Zusammenfassung / Abstract

A number of impressive examples demonstrated the potential of iron catalysts in reductive processes, which could be applicable for industrial purposes. This work highlights applications of reductive iron catalysis for the dehalogenation of organic halides and cross-coupling reactions to form alkylarene and styrene derivatives.

We set out to investigate iron-catalyzed cross-coupling strategies, which obviate the need for expensive catalysts and reagents. Furthermore, we aimed at the utilization of challenges substrates, such as sec. alkyl chlorides and alkenyl acetates. Among alkyl halides, chlorides are most attractive due to their low molecular weight, price, and availability from alcohol substitution reactions. Oxygen-based electrophiles represent particularly attractive coupling partners due to the ubiquitous presence of carbonyl compounds in nature and organic synthesis.

Furthermore, this work revolves around the development of iron-catalyzed hydrodehalogenations of organic halides under mild conditions. The directing –I/+M-effect of halides is key to many electrophilic aromatic substitutions. Halides are also being extensively used as cheap and abundant protective groups in industrial processes. However, most of the methods that have been reported for the reductive dehalogenation exhibit low environmental compatibility and low operational simplicity.