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

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.

SUBMITTER: Bokoskie T

PROVIDER: S-EPMC6822118 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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

Bokoskie Treyvon T Cunningham Christopher C Kornman Cory C Kesharwani Tanay T Pattabiraman Mahesh M

ACS omega 20191017 18

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 ...[more]

PMID: 31681890

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