Reactivity of arynes toward functionalized alkenes: intermolecular Alder-ene vs. addition reactions. Issue 14 (15th June 2018)

• Record Type: Journal Article
• Authors: Gupta, Saswata; Xie, Peipei; Xia, Yuanzhi; Lee, Daesung
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 14(2018)
• Page Start: 2208
• Page End: 2213
• Publication Date: 2018-06-15
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00470f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The selectivity between two different manifolds of reactions of arynes reacting with functionalized alkenes is described. 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.