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Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts
Journal article   Open access   Peer reviewed

Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts

Treyvon Bokoskie, Christopher Cunningham, Cory Kornman, Tanay Kesharwani and Mahesh Pattabiraman
ACS Omega, Vol.4(18), pp.17830-17836
10/29/2019
PMCID: PMC6822118
PMID: 31681890
Web of Science ID: WOS:000493751800024

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Abstract

Iodocyclization of 2-alkynylanisoles is an efficient route for synthesizing substituted benzofurans. Reaction efficiency with copper(II) sulfate and sodium iodide in an aqueous slurry under mild conditions is a manifold higher than in organic solvents. Water-soluble hosts of the cyclodextrin family solubilize the compounds in aqueous media and affect the reaction efficiency through conformation control and steric interactions. Computational chemistry and spectral titration provide information on the host-guest complex structure and insight into the mechanistic basis of the observed effects.
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