Iron-catalyzed radical Markovnikov hydrohalogenation and hydroazidation of alkenes

Jonas Elfert, Nils Lennart Frye, Isabel Rempel, Constantin Gabriel Daniliuc and Armido Studer ()
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Jonas Elfert: Universität Münster
Nils Lennart Frye: Universität Münster
Isabel Rempel: Universität Münster
Constantin Gabriel Daniliuc: Universität Münster
Armido Studer: Universität Münster

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract We herein report radical hydroazidation and hydrohalogenation of mono-, di- and trisubstituted alkenes through iron catalysis. The alkene moiety that often occurs as a functionality in natural products is readily transformed into useful building blocks through this approach. Commercially available tosylates and α-halogenated esters are used as radical trapping reagents in combination with silanes as reductants. The reported radical Markovnikov hydroazidation, hydrobromination, hydrochlorination, and hydroiodination occur under mild conditions. These hydrofunctionalizations are valuable and practical alternatives to ionic hydrohalogenations with the corresponding mineral acids that have to be run under harsher acidic conditions, which diminishes the functional group tolerance. Good to excellent diastereoselectivities can be obtained for the hydrofunctionalization of cyclic alkenes.

Date: 2024
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DOI: 10.1038/s41467-024-51706-x

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