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PHOTO-BORAD

Boron chemistry in a new light: exploring the radical reactivity of boronate complexes through photochemical strategies

Total Cost €

0

EC-Contrib. €

0

Partnership

0

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 PHOTO-BORAD project word cloud

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

alkyl    solid    electrophilic    oxidise    synthetic    believe    stereospecific    mild    irradiation    employ    forging    vinyl    transformation    host    complexes    esters    carefully    scientific    structures    boron    harbouring    pillars    groups    molecule    merge    reported    academic    seek    reactive    radicals    species    ing    thereby    researcher    adjacent    mechanistic    leaving    laying    metallate    trigger    react    chemistry    combining    previously    versatile    enantioenriched    proposing    readily    unconnected    organic    boronate    tremendously    creation    radical    transformations    reactions    group    last    migration    transfer    foundations    endeavour    suite    visible    boronic    cycle    oxidation    intermediate    starting    network    chemical    normally    physical    emerge    decade    chiral    scope    involve    methodology    create    rearrangement    light    bonds    photoredox    positions    emerged    rearrangements    community    links    synthesis    fundamental    catalysis    exploited   

Project "PHOTO-BORAD" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITY OF BRISTOL 

Organization address
address: BEACON HOUSE QUEENS ROAD
city: BRISTOL
postcode: BS8 1QU
website: www.bristol.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 http://www.chm.bris.ac.uk/org/aggarwal/research.php
 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 2017-03-01   to  2019-02-28

 Partnership

Take a look of project's partnership.

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

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 Project objective

In the last decade photoredox reactions have emerged as tremendously versatile processes for organic synthesis, enabling reactive radical species to be generated at specific positions in an organic molecule under very mild conditions (visible-light irradiation). Over the same decade the host group have developed a suite of transformations exploiting the fundamental chemistry of boron, many of which involve 1,2-metallate rearrangement of boronate complexes. We now seek to merge these two major pillars of synthetic methodology, which are currently unconnected, to create a new field which we believe has significant potential for organic synthesis. We propose to react electrophilic radicals generated through photoredox catalysis with vinyl boronate complexes. Oxidation of the resulting intermediate radical during the photoredox cycle will trigger 1,2-alkyl migration, creating new C-C and C-B bonds. 1,2-Metallate rearrangements normally employ leaving groups adjacent to boron but here we are proposing to oxidise a radical adjacent to a boronate to achieve the same transformation, a process that has not been previously reported. 1,2-Metallate rearrangements are stereospecific, and this will be exploited in the creation of enantioenriched products starting from readily available chiral boronic esters. The scope of the process will be carefully investigated, and mechanistic studies will be carried out using advanced physical/chemical methods, thereby laying solid foundations for the development of this new field. By combining two major fields of endeavour, novel chemistry will emerge with new structures harbouring novel properties for exploitation. Furthermore this project will enable significant knowledge transfer between host and researcher, while forging new academic network links within the scientific community.

 Publications

year authors and title journal last update
List of publications.
2018 Mattia Silvi, Raffael Schrof, Adam Noble, Varinder K. Aggarwal
Enantiospecific Three-Component Alkylation of Furan and Indole
published pages: 4279-4282, ISSN: 0947-6539, DOI: 10.1002/chem.201800527
Chemistry - A European Journal 24/17 2019-09-02
2017 Mattia Silvi, Christopher Sandford, Varinder K. Aggarwal
Merging Photoredox with 1,2-Metallate Rearrangements: The Photochemical Alkylation of Vinyl Boronate Complexes
published pages: 5736-5739, ISSN: 0002-7863, DOI: 10.1021/jacs.7b02569
Journal of the American Chemical Society 139/16 2019-09-02
2018 Mattia Silvi, Paolo Melchiorre
Enhancing the potential of enantioselective organocatalysis with light
published pages: 41-49, ISSN: 0028-0836, DOI: 10.1038/nature25175
Nature 554/7690 2019-09-02

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