# New Organoboron based Methods and Strategies for Organic Synthesis

> **NIH NIH R35** · UNIV OF NORTH CAROLINA CHAPEL HILL · 2021 · $361,040

## Abstract

Project Summary/Abstract
The efficient and stereoselective preparation of chiral organic molecules is vitally important to the development
of new therapeutic agents. However, despite significant progress, many desirable complex 2D and 3D molecular
scaffolds remain difficult to access or are inefficiently prepared. Consequently, development of new
transformations that provide synthetic chemists with strategic bond disconnections that facilitate de novo
approaches to organic synthesis is of great importance. In addition, such methods should be robust, practical,
allow the preparation of useful amounts of material, and ideally employ readily available starting materials. The
aim of this MIRA grant is the conversion of an NIGMS funded project with a long-term goal that broadly seeks to
develop and exploit new, practical, and efficient stereoselective new technologies for organic synthesis of
molecular scaffolds of biological importance that are otherwise difficult to access, or inefficiently prepared via
current processes. To this end, we are interested in developing transformations that leverage the broad chemical
reactivity of boron-stabilized chemical synthons for complex molecule synthesis. This approach is attractive
because reactions of such intermediates permit novel bond constructions and simultaneous installation of a
synthetically desirable boron moiety. The proposed studies described in this program will further our expanding
studies of catalytic stereoselective C–C bond forming reactions with organoboron reagents. These readily
accessible reagents merge powerful bond forming reactivity with broad synthetic utility, to deliver versatile
organic compounds of notable significance for fragment-based drug discovery. Building off our previous work,
we are developing new catalytic C–C, C–N, and C–X bond forming methods for the synthesis of chiral amines,
alcohols, and aromatic structures, with a particular focus on examples that contain quaternary carbon
stereogenic centers. We envision that chiral metal nucleophiles can be accessed by enantioselective
transmetalation of readily accessible achiral organodiboron reagents. The resultant nucleophilic species can
engage in a number of enantioselective reactions with various C=O, C=N, C–X electrophiles. We also aim to
target the generation and utility of novel boron-functionalized synthons by metal-free Lewis base catalysis for
reactions with electrophiles that are difficult to achieve via transition metal catalysis. Importantly, enantioselective
variants of these unknown reactions will herein be explored. Furthermore, new nucleophilic aromatic substitution
reactions of aromatic and heteroaromatic compounds with organoboron carbon nucleophiles will be developed
that operate under metal-free conditions. Overall, by exploring synthetic reactions of organoborons, these studies
in methods development will introduce new transformations and strategies that will streamline synthetic chemists'
approaches to ...

## Key facts

- **NIH application ID:** 10200330
- **Project number:** 1R35GM141558-01
- **Recipient organization:** UNIV OF NORTH CAROLINA CHAPEL HILL
- **Principal Investigator:** Simon John Meek
- **Activity code:** R35 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2021
- **Award amount:** $361,040
- **Award type:** 1
- **Project period:** 2021-05-01 → 2026-03-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10200330

## Citation

> US National Institutes of Health, RePORTER application 10200330, New Organoboron based Methods and Strategies for Organic Synthesis (1R35GM141558-01). Retrieved via AI Analytics 2026-05-22 from https://api.ai-analytics.org/grant/nih/10200330. Licensed CC0.

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