TY - JOUR
T1 - Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts
AU - Bokoskie, Treyvon
AU - Cunningham, Christopher
AU - Kornman, Cory
AU - Kesharwani, Tanay
AU - Pattabiraman, Mahesh
N1 - Funding Information:
This research was supported by the ACS-Petroleum Research Fund (#54862-UR4) and the Research Corporation for Science Advancement for the Cottrell College Science Award (ID 23248). M.P. is thankful for the support from the UNK’s Office of Sponsored Programs. T.K. and C.C. are grateful for generous support provided by the University of West Florida (UWF), the UWF’s Office of Research and Sponsored Programs and Office of Undergraduate Research. C.C. is thankful to the National Institute of General Medical Sciences of the National Institutes of Health under grant no. 1T34GM110517-01. This content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health.
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2019/10/29
Y1 - 2019/10/29
N2 - 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.
AB - 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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U2 - 10.1021/acsomega.9b02466
DO - 10.1021/acsomega.9b02466
M3 - Article
C2 - 31681890
AN - SCOPUS:85073878292
SN - 2470-1343
VL - 4
SP - 17830
EP - 17836
JO - ACS Omega
JF - ACS Omega
IS - 18
ER -