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Issue 10, 2017
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α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

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Abstract

Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented. These cascades proceed via electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the key step. Alkynyl migration leads to a ketyl radical anion that sustains the chain as a single electron transfer reducing reagent.

Graphical abstract: α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

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Publication details

The article was received on 15 May 2017, accepted on 02 Aug 2017 and first published on 04 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02175E
Citation: Chem. Sci., 2017,8, 6888-6892
  • Open access: Creative Commons BY license
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    α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

    X. Tang and A. Studer, Chem. Sci., 2017, 8, 6888
    DOI: 10.1039/C7SC02175E

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