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

Treyvon Bokoskie, Christopher Cunningham, Cory Kornman, Tanay Kesharwani, Mahesh Pattabiraman

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)17830-17836
Number of pages7
JournalACS Omega
Volume4
Issue number18
DOIs
StatePublished - Oct 29 2019

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Benzofurans
Sodium Iodide
Computational chemistry
Water
Cyclodextrins
Titration
Organic solvents
Conformations
Copper
Sodium
Sulfates

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. / Bokoskie, Treyvon; Cunningham, Christopher; Kornman, Cory; Kesharwani, Tanay; Pattabiraman, Mahesh.

In: ACS Omega, Vol. 4, No. 18, 29.10.2019, p. 17830-17836.

Research output: Contribution to journalArticle

Bokoskie, Treyvon ; Cunningham, Christopher ; Kornman, Cory ; Kesharwani, Tanay ; Pattabiraman, Mahesh. / Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. In: ACS Omega. 2019 ; Vol. 4, No. 18. pp. 17830-17836.
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