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

Treyvon Bokoskie | Zendy; Christopher Cunningham | Zendy; Cory T. Kornman | Zendy; Tanay Kesharwani | Zendy; Mahesh Pattabiraman | Zendy

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

Author(s) -

Treyvon Bokoskie,

Christopher Cunningham,

Cory T. Kornman,

Tanay Kesharwani,

Mahesh Pattabiraman

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b02466

Subject(s) - aqueous solution , steric effects , chemistry , supramolecular chemistry , cyclodextrin , iodide , titration , combinatorial chemistry , organic chemistry , molecule

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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