Aldehyde addition Manuscript.pdf (621.42 kB)

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

Download (621.42 kB)
journal contribution
posted on 14.01.2019 by Saswata Gupta, Peipei Xie, Yuanzhi Xia, Daesung Lee
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.

Categories

Keyword(s)

Funding

Financial Support from NSF (1361620, DL), Tacoma Technology, and NSFC (2137278 and 21572163, YX) and the mass spectrometry facility at UIUC is greatly acknowledged.

History

Publisher Statement

Copyright @ Royal Society of Chemistry

Citation

Gupta, S., Xie, P., Xia, Y., & Lee, D. (2018). Reactivity of arynes toward functionalized alkenes: Intermolecular Alder-ene: Vs. addition reactions. Organic Chemistry Frontiers, 5(14), 2208-2213. doi:10.1039/c8qo00470f

Publisher

Royal Society of Chemistry

Language

en_US

issn

2052-4110

Issue date

15/06/2018

Exports

Categories

Keyword(s)

Exports