Yes / Herein, we report a catalyst-free ‘click’ reaction: metal-free [2 + 2]
cycloaddition–retro-electrocyclisation (CA–RE) of arylynamines
with the sluggish acceptor tetracyanoquinodimethane (TCNQ) to
provide orthogonal electron-push–pull light-harvesting small
molecules: N-heterocyclic dicyanoquinodimethane-substituted
methylene malononitriles. Ynamines are reactive alkynes and tend
to induce over-reactions with the CA–RE adducts. The reactivity of
arylynamines was balanced properly by ensuring the electrondensity of the nitrogen atom was delocalised more over the aromatic rings than the triple bond. / This work was supported by Guangxi Natural Science Foundation (2020JJA120032). / Research Development Fund Publication Prize Award winner, April 2022.
| Identifer | oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/19083 |
| Date | 24 July 2022 |
| Creators | Huang, S., Ma, J., Yi, Y., Li, M., Cai, P., Wu, Na (Anna) |
| Source Sets | Bradford Scholars |
| Language | English |
| Detected Language | English |
| Type | Article, Accepted manuscript |
| Rights | © The Royal Society of Chemistry 2022. Reproduced in accordance with the publisher's self-archiving policy., Unspecified |
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