Harnessing the polarizability of conjugated alkynes toward [2 + 2] cycloaddition, alkenylation, and ring expansion of indoles

Pradhan, Tapas R., Kim, Hong Won and Park, Jin Kyoon 2018. Harnessing the polarizability of conjugated alkynes toward [2 + 2] cycloaddition, alkenylation, and ring expansion of indoles. Organic Letters 20 (17) , 5286–5290. 10.1021/acs.orglett.8b02230

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Abstract

Reported is the utilization of electronically biased conjugated alkynes in the development of highly diastereo- and regioselective dearomative [2 + 2] cycloadditions, alkenylations, and ring expansions of electron-rich indoles. Regioselective protonations of cross- and linear-conjugated alkynes were found to be crucial for accessing various cyclobutene-fused indoline and alkenylated indole derivatives. Furthermore, the facile ring expansion of [2 + 2] keto adducts, which were successfully synthesized from ynones, provided 1H-benzo[b]azepine scaffolds.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	American Chemical Society
ISSN:	1523-7060
Last Modified:	26 Jan 2024 14:45
URI:	https://orca.cardiff.ac.uk/id/eprint/165582

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