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Issue 14, 2018
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Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions

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Abstract

The selectivity between two different manifolds of reactions of arynes reacting with functionalized alkenes is described. Arynes generated from bis-1,3-diynes react with various trisubstituted and 1,1-disubstituted alkenes including methallyl amine, prenyl azide, and methacrylic acid, providing mainly addition products of the polar heteroatom functionalities over the Alder-ene products of the alkene segment. The selectivity, however, intricately depends on the substituent pattern of the alkene. Except for the most reactive 2-propenyl group-containing aldehyde, α,β-unsaturated aldehydes generally participated in an addition reaction, generating chromene derivatives.

Graphical abstract: Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions

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Publication details

The article was received on 12 May 2018, accepted on 08 Jun 2018 and first published on 15 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00470F
Citation: Org. Chem. Front., 2018,5, 2208-2213
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    Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions

    S. Gupta, P. Xie, Y. Xia and D. Lee, Org. Chem. Front., 2018, 5, 2208
    DOI: 10.1039/C8QO00470F

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