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NCR

Visible Light-Mediated Synthesis of Nitrogen-Centered Radicals: New Reactivity via Photoredox Catalysis and Electron-Transfer Complexes

Total Cost €

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EC-Contrib. €

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Partnership

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Project "NCR" data sheet

The following table provides information about the project.

Coordinator
THE UNIVERSITY OF MANCHESTER 

Organization address
address: OXFORD ROAD
city: MANCHESTER
postcode: M13 9PL
website: www.manchester.ac.uk

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 https://www.leonorigroup.com/
 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-2015
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2017
 Duration (year-month-day) from 2017-02-01   to  2019-01-31

 Partnership

Take a look of project's partnership.

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

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 Project objective

Nitrogen-containing molecules are among the most important class of compounds due to their relevance as medicines, agrochemicals, organic materials and dyes. Nitrogen-centered-radicals are a class of very versatile synthetic intermediates with great potential in the synthesis of N-containing molecules. However, to date, difficulties associated to their generation have severely limited their use and exploitation. Here we propose the development of two conceptually novel and general ways to prepare Nitrogen-centered radicals using visible light as sustainable and inexpensive source of energy. These processes will capitalize on recent developments in the host group that has disclosed the use of easy-to-make aryl oximes for the organocatalytic generation of iminyl radicals. This proposal seeks to substantially expand this visible light chemistry through the development of methods for the generation and use of any known Nitrogen-centered radical. The power of this approach will be demonstrated by the short synthesis of the complex molecule legionaminic acid, responsible for the spread of hospital-acquired infections. Furthermore, these methods will be integrated with other reaction platforms that, taking advantage of visible light as source of energy, will engage the Nitrogen-centered radical in new reactivity modes, to allow novel and powerful multicomponent reactions.

Through the use of this strategy, the rapid construction of many relevant and complex N-containing molecules will be possible. The development of such an innovative and ambitious project at the University of Manchester will be facilitated by generating, transferring, sharing and disseminating knowledge, and will enhance my career development following the training plan envisioned.

 Publications

year authors and title journal last update
List of publications.
2019 Alessandro Ruffoni, Fabio Juliá, Thomas D. Svejstrup, Alastair J. McMillan, James J. Douglas, Daniele Leonori
Practical and regioselective amination of arenes using alkyl amines
published pages: 426-433, ISSN: 1755-4330, DOI: 10.1038/s41557-019-0254-5
Nature Chemistry 11/5 2019-10-14
2017 Daniel Fernandez Reina, Alessandro Ruffoni, Yasair S. S. Al-Faiyz, James J. Douglas, Nadeem S. Sheikh, Daniele Leonori
Visible-Light-Mediated Reactions of Electrophilic Radicals with Vinyl and Allyl Trifluoroborates
published pages: 4126-4130, ISSN: 2155-5435, DOI: 10.1021/acscatal.7b01120
ACS Catalysis 7/6 2019-10-14
2017 Thomas D. Svejstrup, Alessandro Ruffoni, Fabio Juliá, Valentin M. Aubert, Daniele Leonori
Synthesis of Arylamines via Aminium Radicals
published pages: 14948-14952, ISSN: 1433-7851, DOI: 10.1002/anie.201708693
Angewandte Chemie International Edition 56/47 2019-10-14
2019 David C. Marcote, Rosie Street-Jeakings, Elizabeth Dauncey, James J. Douglas, Alessandro Ruffoni, Daniele Leonori
Photoinduced decarboxylative azidation of cyclic amino acids
published pages: 1839-1842, ISSN: 1477-0520, DOI: 10.1039/c8ob02702a
Organic & Biomolecular Chemistry 17/7 2019-10-14

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