# Dearomative Functionalization with Arenophiles

> **NIH NIH R01** · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · 2023 · $175,943

## Abstract

PROJECT SUMMARY
 The objective of the work of the parent grant is to provide new chemical transformations and strategies
that will selectively introduce functionality and, consequently, greatly expand the dearomative chemical toolbox.
 Small, heteroatom-containing complex molecules are common motifs of biological (as well as
pharmaceutical and agrochemical) relevance and are highly desired in medicinal chemistry, but they are also
often difficult to access. Selective transformations of aromatic compounds could provide a more direct route to
such desirable targets; however, the many challenges associated with dearomative functionalization have left
these types of reactions widely underdeveloped. We strive to address this need by bridging the gap between
dearomatization and alkene chemistry. Fundamentally, the goal of this proposal is to access desirable structural
motifs from simple aromatic compounds by developing dearomative functionalizations using small molecules –
arenophiles – that enable reactions of isolated alkenes in an arene substrate. Additionally, arenophiles, in
combination with transition metal catalysis, provide uniquely reactive substrates for nucleophilic substitution
reactions, and could enable the rapid synthesis of a diverse range of aminofunctionalized alicyclic compounds.
We have prepared a series of potent anticancer natural products and antibiotics and are currently preparing
analogues for SAR studies as well as designing prodrugs with improved pharmacokinetics properties. The
instrument, UHPLC-MS, to be purchased by funds from this Supplement will allow us for analysis of these highly
polar compounds and will greatly facilitate these studies.

## Key facts

- **NIH application ID:** 10794085
- **Project number:** 3R01GM122891-06S1
- **Recipient organization:** UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN
- **Principal Investigator:** David Sarlah
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2023
- **Award amount:** $175,943
- **Award type:** 3
- **Project period:** 2017-07-15 → 2026-06-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10794085

## Citation

> US National Institutes of Health, RePORTER application 10794085, Dearomative Functionalization with Arenophiles (3R01GM122891-06S1). Retrieved via AI Analytics 2026-05-25 from https://api.ai-analytics.org/grant/nih/10794085. Licensed CC0.

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