Book Chapter10.1016/B978-0-08-097742-3.00725-4
7.21 Addition Reactions with Formation of CarbonHalogen Bonds
U. Hennecke,C. Rösner,T. Wald,T. Robert,M. Oestreich +4 more
- 01 Feb 2014
- pp 638-691
12
TL;DR: In this chapter, the focus is placed on the most significant developments of the past two decades with emphasis on methods that exhibit either broad substrate scope or unique entries into classes of compounds relevant to complex molecule synthesis.
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Abstract: Halogenation reactions of alkenes are useful tools in synthetic organic chemistry. These provide access to a broad range of various structural motifs, and the incorporation of one or two halogen atoms into the molecule allows for subsequent functional group manipulation. In this chapter, the focus is placed on the most significant developments of the past two decades with emphasis on methods that exhibit either broad substrate scope or unique entries into classes of compounds relevant to complex molecule synthesis. Besides dihalogenation and hydrofluorination reactions, the important areas of oxy-, amino-, and carbohalogenation reactions are discussed with a strong focus on recent developments in stereoselective method.
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Citations
Mechanisms in Iodine Catalysis.
TL;DR: The experimental basis for the proposed modes of activation for iodine catalysis is summarized and typical iodine-catalyzed reactions are analyzed to gain more insights into the underlying reaction mechanisms.
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Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes.
Christian Rösner,Ulrich Hennecke +1 more
TL;DR: An efficient method for the halocyclization ofcyclopropanes has been developed and excellent induced diastereoselectivities can be observed in cyclopropane derivatives with a preexisting stereocenter.
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Stable Bromiranium Ions with Weakly-Coordinating Counterions as Efficient Electrophilic Brominating Agents
Christoph Ascheberg,Jonathan Bock,Florenz Buß,Christian Mück-Lichtenfeld,Constantin G. Daniliuc,Klaus Bergander,Fabian Dielmann,Ulrich Hennecke +7 more
TL;DR: It is shown that sterically demanding bromiranium ions with weakly coordinating counterions are highly reactive electrophilic brominating agents that are stable under ambient conditions and can be applied in Electrophilic halogenations of alkenes as well as heteroatoms.
21
Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release
TL;DR: This metal-free, catalytic chemo-, regio-, and diastereoselective bromochlorination of alkenes and alkynes exhibits excellent site selectivity in polyunsaturated systems and provides access to a wide variety of vicinal brom Cochlorides with up to >20:1 regio- and diastaoselectivity.
19
Regioselective Chlorolactonization of Styrene-Type Carboxylic Esters and Amides via PhICl2-Mediated Oxidative C-O/C-Cl Bond Formations.
TL;DR: A metal-free regioselective intramolecular chlorolactonization process was proposed to involve a PhICl2-mediated oxidative C-O bond formation followed by C-Cl bond formation.
10
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