Award Abstract # 2243793
RUI: Development of New Reagents and Synthetic Methodologies Based on Hypervalent Iodine Chemistry

NSF Org: CHE
Division Of Chemistry
Recipient: REGENTS OF THE UNIVERSITY OF MINNESOTA
Initial Amendment Date: April 28, 2023
Latest Amendment Date: April 28, 2023
Award Number: 2243793
Award Instrument: Standard Grant
Program Manager: John C. Jewett
jjewett@nsf.gov
 (703)292-5373
CHE
 Division Of Chemistry
MPS
 Directorate for Mathematical and Physical Sciences
Start Date: July 1, 2023
End Date: June 30, 2026 (Estimated)
Total Intended Award Amount: $357,254.00
Total Awarded Amount to Date: $357,254.00
Funds Obligated to Date: FY 2023 = $357,254.00
History of Investigator:
  • Viktor Zhdankin (Principal Investigator)
    vzhdanki@d.umn.edu
Recipient Sponsored Research Office: University of Minnesota Duluth
1049 UNIVERSITY DRIVE 209 DARLAND
DULUTH
MN  US  55812-3011
(218)726-7582
Sponsor Congressional District: 08
Primary Place of Performance: University of Minnesota Duluth
1035 UNIVERSITY DR RM 133
DULUTH
MN  US  55812-3031
Primary Place of Performance
Congressional District:
08
Unique Entity Identifier (UEI): LPCTM8BS8NF3
Parent UEI:
NSF Program(s): Chemical Synthesis
Primary Program Source: 01002324DB NSF RESEARCH & RELATED ACTIVIT
Program Reference Code(s): 8037, 9229
Program Element Code(s): 687800
Award Agency Code: 4900
Fund Agency Code: 4900
Assistance Listing Number(s): 47.049

ABSTRACT

With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Viktor V. Zhdankin of the University of Minnesota Duluth (UMD) is studying the development of new reagents and synthetic methodologies based on the organic chemistry of iodine. The project is exploring the preparation and fundamental chemistry of new hypervalent iodine compounds. The ability of hypervalent iodine species to modify organic compounds when coupled with their efficiency and sustainability makes them useful among academic and industrial scientists. This utility is the result of iodine behaving much like a transition metal in many applications. The continued exploration and utilization of these similarities is leading to the development of new useful methodologies for modern organic chemistry. More broadly speaking, this project is at the interface of organic and inorganic chemistry and is well-suited for undergraduate, graduate, and more advanced researchers including researchers in industry. The project is expected to provide high level of education and training for students, many of whom are underrepresented in science.

A broad study of new, metal-free, iodine-mediated reactions and an exploratory search for new and potentially useful hypervalent reagents is proposed. Specific objectives include: (i) the development of pseudocyclic arylbenziodoxaboroles as benzyne precursors and highly efficient electrophilic arylating reagents under neutral, aqueous conditions, (ii) the exploration of 4-iodonium substituted arylboronic acids as para-benzyne precursors, (iii) the study of the synthesis and reactivity of stabilized iodonium derivatives of porphyrins and dipyrromethenes, and (iv) the search for new types of polyvalent iodine compounds that are stabilized by internal halogen bonding. New synthetic methodologies based on these efforts will contribute to the discovery of environmentally benign methods for chemical synthesis as they utilize non-toxic iodine compounds in water as catalysts or as recoverable/recyclable reagents. The successful development of this methodology will have an impact on the areas of science where the synthesis of organic molecules is required, such as in academia and in the pharmaceutical, chemical, and agricultural industries.

This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

PUBLICATIONS PRODUCED AS A RESULT OF THIS RESEARCH

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(Showing: 1 - 10 of 11)
Kumar, Ravi and Dohi, Toshifumi and Zhdankin, Viktor V "Organohypervalent heterocycles" Chemical Society Reviews , v.53 , 2024 https://doi.org/10.1039/d2cs01055k Citation Details
Kumar, Ravi and Zhdankin, Viktor V "Recent progress in hypervalent iodine chemistry" Arkivoc , v.2025 , 2025 https://doi.org/10.24820/ark.5550190.p012.370 Citation Details
Rimi and Uttam, Bhawna and Sharma, Deepansh and Zhdankin, Viktor V and Kumar, Ravi "Pyrazole-tethered isoxazoles: hypervalent iodine-mediated, metal-free synthesis and biological evaluation" Arkivoc , v.2024 , 2025 https://doi.org/10.24820/ark.5550190.p012.328 Citation Details
Huss, Christopher D. and Yoshimura, Akira and Rohde, Gregory T. and Mironova, Irina A. and Postnikov, Pavel S. and Yusubov, Mekhman S. and Saito, Akio and Zhdankin, Viktor V. "Preparation and X-ray Structural Study of Dibenzobromolium and Dibenzochlorolium Derivatives" ACS Omega , v.9 , 2024 https://doi.org/10.1021/acsomega.3c07512 Citation Details
Rimi and Uttam, Bhawna and Zhdankin, Viktor V. and Kumar, Ravi "New IsoxazoleSubstituted Aryl Iodides: MetalFree Synthesis, Characterization and Catalytic Activity" European Journal of Organic Chemistry , v.27 , 2024 https://doi.org/10.1002/ejoc.202301191 Citation Details
Uehara, Daigo and Adachi, Sota and Tsubouchi, Akira and Okada, Yohei and Zhdankin, Viktor V. and Yoshimura, Akira and Saito, Akio "Peptide coupling using recyclable bicyclic benziodazolone" Chemical Communications , v.60 , 2024 https://doi.org/10.1039/d3cc04431a Citation Details
Yoshimura, Akira and Ngo, Kim and Mironova, Irina A and Gardner, Zachary S and Ogura, Nami and Ueki, Akiharu and Yusubov, Mekhman S and Saito, Akio and Zhdankin, Viktor V "Generation of benzyne from aryl benziodoxaborole triflate under aqueous conditions and its reactions with alkyl aryl sulfides" Arkivoc , v.2024 , 2025 https://doi.org/10.24820/ark.5550190.p012.213 Citation Details
Yoshimura, Akira and Ngo, Kim and Mironova, Irina A. and Gardner, Zachary S. and Rohde, Gregory T. and Ogura, Nami and Ueki, Akiharu and Yusubov, Mekhman S. and Saito, Akio and Zhdankin, Viktor V. "Pseudocyclic Arylbenziodoxaboroles as Water-Triggered Aryne Precursors in Reactions with Organic Sulfides" Organic Letters , v.26 , 2024 https://doi.org/10.1021/acs.orglett.4c00197 Citation Details
Yoshimura, Akira and Saito, Akio and Zhdankin, Viktor V. "Recent Progress in Synthetic Applications of Cyclic Hypervalent Iodine(III) Reagents" Advanced Synthesis & Catalysis , v.365 , 2023 https://doi.org/10.1002/adsc.202300275 Citation Details
Yoshimura, Akira and Zhdankin, Viktor_V "Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents" Chemical Reviews , v.124 , 2024 https://doi.org/10.1021/acs.chemrev.4c00303 Citation Details
Zarrabi, N and Zhdankin, V and Krystosek, S and Hughes, G "Synthesis of iodonium ylides stabilized by internal halogen bonding" Abstracts of papers American Chemical Society , 2025 Citation Details
(Showing: 1 - 10 of 11)

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