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Synthesis of sp3-Rich Organofluorine Compounds through Homologation of Boronic Esters

Total Cost €


EC-Contrib. €






 FOOTLOOSE project word cloud

Explore the words cloud of the FOOTLOOSE project. It provides you a very rough idea of what is the project "FOOTLOOSE" about.

bonds    atoms    enantioselective    bond    borylation    sharpening    rewarding    enriched    stereoselective    mediated    attractive    carbamates    modifications    homologation    lithiation    benzoates    exquisite    stone    stability    imparted    temperature    chains    fluorine    dependent    programs    stereochemically    grown    substituted    small    exchange    configuration    pure    enantiospecific    lithiated    lithium    iterative    synthesis    stage    molecule    relative    oxygen    latter    herein    outline    absolute    laboratory    diverse    esters    owing    enantiomerically    chain    assembly    hit    chemical    molecules    either    advantage    landscape    electronegative    made    replacement    primary    containing    chemistry    introduce    preparation    sought    tin    ideal    boronic    deprotonation    secondary    groups    medicinal    organofluorine    conformational    substituents    big    protocol    line    oh    atom    bearing    shown    manner    host    group    compounds    incorporation    formed    closer    time    trifluoromethyl    sparteine    carbon    size    works   

Project "FOOTLOOSE" data sheet

The following table provides information about the project.


Organization address
postcode: BS8 1QU

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country United Kingdom [UK]
 Project website
 Total cost 183˙454 €
 EC max contribution 183˙454 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2016
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2017
 Duration (year-month-day) from 2017-07-27   to  2019-07-26


Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 183˙454.00


 Project objective

Organofluorine compounds are highly sought after owing to diverse and numerous applications that take advantage of the unique properties imparted by the presence of one or more C–F bonds. The chemical stability and conformational landscape of molecules, together with the small size of the fluorine atom, has the made the replacement of a C–H or C–OH bond with a C–F one of the most rewarding modifications during the hit-to-lead stage in medicinal chemistry programs. Because many applications are dependent on the absolute and relative configuration of the fluorine-containing group, methods that can introduce such groups in a stereoselective manner are particularly attractive. The host laboratory has shown that substituted carbon chains can be grown one carbon atom at a time with exquisite control of relative and absolute configuration through iterative homologation of boronic esters with stereochemically-defined lithiated carbamates or benzoates. The latter are formed at low temperature, either through sparteine-mediated enantioselective deprotonation of primary carbamates/benzoates or the enantiospecific deprotonation or tin–lithium exchange of enantiomerically pure secondary carbamates/ benzoates. Although the process works well for extending a carbon chain with incorporation of carbon-based substituents, the incorporation of carbon atoms bearing electronegative substituents, such as oxygen- or fluorine-containing groups, is challenging. Herein we propose a programme of research to investigate the preparation of enantiomerically enriched organofluorine molecules, specifically those containing trifluoromethyl groups, through lithiation–borylation. The challenges outline above would make such a programme the ideal sharpening stone for the further development of lithiation–borylation. Indeed, a protocol that can introduce carbon atoms bearing electronegative groups would bring us a big step closer to assembly-line synthesis being able to make any molecule.


year authors and title journal last update
List of publications.
2018 Roly J. Armstrong, Meganathan Nandakumar, Rafael M. P. Dias, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal
Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer
published pages: 8203-8208, ISSN: 1433-7851, DOI: 10.1002/anie.201804446
Angewandte Chemie International Edition 57/27 2020-04-14

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