# electrochemical dication pool: a new strategy to couple alkenes and abundant nucleophiles

> **NIH NIH R01** · UNIVERSITY OF WISCONSIN-MADISON · 2024 · $302,391

## Abstract

PROJECT SUMMARY/ABSTRACT
Oxidative alkene functionalization reactions are a fundamental class of organic reactions. These reactions
are valuable because they transform readily accessible alkene starting materials into diverse polar functional
groups. However, the design strategies that underpin conventional alkene oxidation reactions require
electrophilic reagents that serve as both the oxidant and the source of the newly installed functional group.
This substantially limits the chemical diversity accessible using these methodologies. A modular approach to
alkene oxidation that directly leverages abundant nucleophiles is a long-standing challenge with no general
solutions.
This proposal is based on a recent discovery from my group that electrochemistry can generate a new class
of dicationic adducts between alkenes and thianthrene that are exceptionally selective dielectrophiles. We will
study how these adducts can be exploited to develop a suite of alkene oxidation reactions that are otherwise
infeasible with modern synthetic tactics. The three specific aims of this research explore distinct but
interwoven aspects of this new reaction platform.
Aim 1. We are advancing a strategy for strained ring synthesis from abundant precursors
Aim 2. We are advancing a modular platform for oxidative alkene heterodifunctionalization
Aim 3. We are advancing a strategy for allylic amine synthesis from abundant precursors
The methods developed through this work each address long-standing challenges in a fundamental class of
organic reactions, alkene oxidations. These new reaction protocols will offer an expanded and diversified pool
of building blocks from which the next generation of drugs and molecular probes will be discovered.

## Key facts

- **NIH application ID:** 10904656
- **Project number:** 5R01GM149674-02
- **Recipient organization:** UNIVERSITY OF WISCONSIN-MADISON
- **Principal Investigator:** Zachary Kimble Wickens
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2024
- **Award amount:** $302,391
- **Award type:** 5
- **Project period:** 2023-08-15 → 2027-05-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10904656

## Citation

> US National Institutes of Health, RePORTER application 10904656, electrochemical dication pool: a new strategy to couple alkenes and abundant nucleophiles (5R01GM149674-02). Retrieved via AI Analytics 2026-05-22 from https://api.ai-analytics.org/grant/nih/10904656. Licensed CC0.

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