Issue 14, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
12 May 2018
Accepted
08 Jun 2018
First published
15 Jun 2018

Org. Chem. Front., 2018,5, 2208-2213

Author version available

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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