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Issue 5, 2018
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Radical-initiated alkene hydroauration as a route to gold(III) alkyls: an experimental and computational study

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Abstract

The hydroauration of functionalised 1-alkenes by the gold(III) hydride (C^NOMe^C)AuH is initiated by organic radicals and proceeds via (C^N^C)Au(II) radical intermediates following a bimolecular outer-sphere mechanism. The outcome of these reactions is determined by the stability of the gold-substituted radicals, and chemoselectivity correlates with the degree of spin delocalisation in the alkylgold radical intermediates. The reaction is sensitive to steric as well as electronic factors; disubstituted alkenes and alkenes that form unstable radicals give product mixtures or are unreactive. As DFT calculations show, the reactions agree well with the calculated reaction enthalpies and the standard free energy change for the reaction of the gold(II) radical with the respective alkene.

Graphical abstract: Radical-initiated alkene hydroauration as a route to gold(iii) alkyls: an experimental and computational study

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Publication details

The article was received on 19 Dec 2017, accepted on 05 Jan 2018 and first published on 12 Jan 2018


Article type: Paper
DOI: 10.1039/C7RA13481A
Citation: RSC Adv., 2018,8, 2795-2803
  • Open access: Creative Commons BY license
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    Radical-initiated alkene hydroauration as a route to gold(III) alkyls: an experimental and computational study

    A. Pintus and M. Bochmann, RSC Adv., 2018, 8, 2795
    DOI: 10.1039/C7RA13481A

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