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

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 main...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2018-01, Vol.5 (14), p.2208-2213
Main Authors: Gupta, Saswata, Xie, Peipei, Xia, Yuanzhi, Lee, Daesung
Format: Article
Language:English
Subjects:
Aldehydes
Alkenes
Methacrylic acid
Organic chemistry
Selectivity
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c8qo00470f