# An electrocatalytic approach to discovering new synthetic transformations

> **NIH NIH R01** · CORNELL UNIVERSITY · 2022 · $129,365

## Abstract

Project Summary
This proposal focuses on uncovering new electrocatalytic technologies that facilitate the synthesis of
bioactive compounds. Improving the synthetic efficiency of medicinally active organic compounds is
crucial to modern biomedical research. Oxidation and reduction reactions are among the most important
and frequently executed processes in organic synthesis. However, our ability to manipulate the oxidation
states of functional groups in complex settings with high efficiency, precision, and minimal waste remains
in a largely nascent stage. Owing to its many distinct characteristics, electrochemistry represents an
attractive approach to meet the prevailing trends in organic synthesis. In particular, electrocatalysis—a
process that integrates electrochemistry and small-molecule catalysis—has the potential to substantially
improve the scope of synthetic electrochemistry and provide a wide range of useful transformations.
Despite its attractive attributes and extensive applications in energy-related fields, electrocatalysis has
been used only sparingly in synthetic organic chemistry. Thus, there exists a clear impetus for inventing
new catalytic strategies to improve the scope of synthetic electrochemistry and provide new platforms for
reaction discovery and synthetic innovations. Toward this end, we developed a new catalytic approach
that combines electrochemistry and redox-metal catalysis for the oxidative difunctionalization of alkenes
to access a diverse array of vicinally functionalized structures. These promising results led us to envision
that electrocatalytic strategies will ultimately emerge as powerful tools for solving a wide range of long-
standing synthetic problems. Each of the projects described herein applies our general strategy of
electrocatalysis to address a prominent challenge in organic synthesis. Specifically, we aim to develop
reactions such as the chlorophosphonylation, chloro(hetero)arylation, and fluorotrifluoromethylation of
alkenes; ring-opening functionalization of cycloalkanols to make remotely functionalized ketones;
intermolecular 1,1-difunctionalization of isonitriles to make imidoyl chlorides; and C–N coupling via the
activation of C–H bonds. These oxidative transformations are either currently unknown or have significant
limitations in reaction scope, efficiency, or selectivity. We will also carry out in-depth studies using
canonical physical organic and electrochemical techniques to gain insights into the reaction mechanisms.
The development and mechanistic understanding of these proposed transformations will represent
significant advances for the field of organic synthesis.

## Key facts

- **NIH application ID:** 10677350
- **Project number:** 3R01GM130928-05S1
- **Recipient organization:** CORNELL UNIVERSITY
- **Principal Investigator:** Song Lin
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2022
- **Award amount:** $129,365
- **Award type:** 3
- **Project period:** 2018-09-20 → 2023-08-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10677350

## Citation

> US National Institutes of Health, RePORTER application 10677350, An electrocatalytic approach to discovering new synthetic transformations (3R01GM130928-05S1). Retrieved via AI Analytics 2026-05-24 from https://api.ai-analytics.org/grant/nih/10677350. Licensed CC0.

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