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Issue 39, 2019
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Alkynylation of radicals: spotlight on the “Third Way” to transfer triple bonds

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Abstract

The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensively investigated leading to new disconnections to introduce versatile triple bonds into organic compounds. Nowadays, such processes are important alternatives to classical nucleophilic and electrophilic alkynylations. Efficient alkyne transfer reagents, in particular arylsulfones and hypervalent iodine reagents were introduced. Direct alkynylation, as well as cascade reactions, were subsequently developed. If relatively harsh conditions were required in the past, a new era began with progress in photoredox and transition metal catalysis. Starting from various radical precursors, alkynylations under very mild reaction conditions were rapidly discovered. This review covers the evolution of radical alkynylation, from its emergence to its current intensive stage of development. It will focus in particular on improvements for the generation of radicals and on the extension of the scope of radical precursors and alkyne sources.

Graphical abstract: Alkynylation of radicals: spotlight on the “Third Way” to transfer triple bonds

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Publication details

The article was received on 19 Jun 2019, accepted on 12 Aug 2019 and first published on 13 Aug 2019


Article type: Perspective
DOI: 10.1039/C9SC03033F
Chem. Sci., 2019,10, 8909-8923
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Alkynylation of radicals: spotlight on the “Third Way” to transfer triple bonds

    F. Le Vaillant and J. Waser, Chem. Sci., 2019, 10, 8909
    DOI: 10.1039/C9SC03033F

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

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