# Selective Chemical Synthesis and Catalysis Enabled by Single-Electron Oxidation of Aromatic N-oxides

> **NIH NIH R35** · INDIANA UNIVERSITY INDIANAPOLIS · 2024 · $337,390

## Abstract

Project Summary/Abstract
The straightforward laboratory preparation of structural motifs commonly found in therapeutic agents in a
selective fashion and utilizing readily available chemicals is a major driving force in the development of new
synthetic strategies and catalysis. In our laboratory, we have adopted synthesis and catalysis development via
unconventional single-electron transfer chemistry of aromatic N-oxides, readily accessible, tunable, and versatile
compounds. Our long-term research goal is to develop and understand the single-electron transfer process of
aromatic N-oxides that could offer new chemical space and access to synthesis and catalysis enabling discovery
and innovation across synthetic and biological systems. The five-year research program will lead to a greater
understanding of the currently underdeveloped single-electron transfer chemistry of aromatic N-oxides, and it is
expected to broadly expand its use as a new and practical means of accessing new chemical space for synthetic
methodology and catalysis development. The outcomes of the proposed research will have the potential to be
transformational in that they will 1) aid in ushering in the future development of single-electron chemistry of
aromatic N-oxides; 2) expedite the design, development and manufacture of medicines to manage and treat
diseases; 3) conceptualize catalytic and selective transformations of societal importance, thereby moving
synthesis and therapeutic development vertically.
 Based on our research accomplishments and exciting preliminary data we have obtained in the arenas of 1)
vinyl radical chemistry for concise and efficient synthesis of complex molecules, and 2) hydrogen-atom transfer
(HAT) catalysis for selective C-H functionalization. The proposed research in Area 1 will establish an original
and innovative strategy utilizing readily available alkynes and pyridine N-oxides for the facile generation of -
oxypyridinium vinyl radical to unleash its synthetic potential. Such a strategy will enable the development of a
variety of radical cascade reactions leading to the discovery of new transformations and synthetic methods that
could not be accomplished by conventional methods. This contribution is expected to broadly expand the
synthetic applications of vinyl radical mediated reactions and it will provide new synthetic opportunities for the
design and development of new clinical agents using alkynes for the construction of a wide range of carbo- and
hetero-cycles, and carbonyl functionalities. Our proposed research in Area 2 is expected to establish an
innovative and modular catalyst system for regio- and stereoselective C-H functionalization by developing
aromatic N-oxide based photoinduced HAT catalysts with effective reactivity towards unactivated C(sp3)−H
bonds. The proposed multiple strategies incorporated with experimental and computational studies, including
catalyst structure development, cooperative approach, and bifunctional catalyst...

## Key facts

- **NIH application ID:** 10888348
- **Project number:** 5R35GM150542-02
- **Recipient organization:** INDIANA UNIVERSITY INDIANAPOLIS
- **Principal Investigator:** Yongming Deng
- **Activity code:** R35 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2024
- **Award amount:** $337,390
- **Award type:** 5
- **Project period:** 2023-07-15 → 2028-04-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10888348

## Citation

> US National Institutes of Health, RePORTER application 10888348, Selective Chemical Synthesis and Catalysis Enabled by Single-Electron Oxidation of Aromatic N-oxides (5R35GM150542-02). Retrieved via AI Analytics 2026-05-24 from https://api.ai-analytics.org/grant/nih/10888348. Licensed CC0.

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