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PHAROS SIGNED

Photocatalytic Generation of CarbAnions for Organic Synthesis

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EC-Contrib. €

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Project "PHAROS" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITAET REGENSBURG 

Organization address
address: UNIVERSITATSSTRASSE 31
city: REGENSBURG
postcode: 93053
website: http://www.uni-regensburg.de/

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 Germany [DE]
 Total cost 2˙458˙200 €
 EC max contribution 2˙458˙200 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2016-ADG
 Funding Scheme ERC-ADG
 Starting year 2017
 Duration (year-month-day) from 2017-09-01   to  2022-08-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITAET REGENSBURG DE (REGENSBURG) coordinator 2˙458˙200.00

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 Project objective

Light is a fascinating reagent for chemistry as it provides energy to drive reactions, but leaves no trace. In visible light photoredox catalysis the initial electron transfer from the excited dye to a substrate yields radical anion or radical intermediates, which dominate the subsequent chemistry. Carbanions, which are the most important nucleophiles in organic chemistry, are typically not available from photocatalysis. The project PHAROS aims to overcome the current limitation of visible light photocatalysis to radical chemistry and extend its use to carbon nucleophiles. To obtain carbanions for organic synthesis using visible light, we propose three specific project tasks:

1) We develop the next generation of visible light photocatalysts extending the current energetic limit of bond activation required for carbanion generation. This task is based on our recently developed consecutive photoinduced electron transfer (conPET) strategy accumulating the energy of more than one photon for synthesis. Now, the reduction power is further increased reaching potentials of alkali metals and allowing sequential two-electron transfers as needed for preparing carbanions.

2) This technology is then used to generate carbanions from neutral starting materials by visible light photoinduced one- or two-electron transfer. The concept allows a light-driven synthetic carbanion chemistry without the stoichiometric use of reducing reagents, such as magnesium, zinc or lithium.

3) Faster and cleaner reactions, longer catalyst lifetimes and selective photocatalytic sequences are achieved by sensitized photocatalysts and pulsed light excitation. This will enhance the overall energy efficiency of photoredox catalysis facilitating practical applications.

The energy of visible light provides the redox energy to generate carbanions for organic synthesis and thereby broadens the synthetic use of the most abundant and sustainable energy source on earth, visible light.

 Publications

year authors and title journal last update
List of publications.
2019 Anamitra Chatterjee, Burkhard König
Birch‐Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
published pages: 14289-14294, ISSN: 1433-7851, DOI: 10.1002/anie.201905485
Angewandte Chemie International Edition 58/40 2020-04-24
2019 Indrajit Ghosh, Jagadish Khamrai, Aleksandr Savateev, Nikita Shlapakov, Markus Antonietti, Burkhard König
Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
published pages: 360-366, ISSN: 0036-8075, DOI: 10.1126/science.aaw3254
Science 365/6451 2020-04-24
2019 Karsten Donabauer, Mitasree Maity, Anna Lucia Berger, Gregory S. Huff, Stefano Crespi, Burkhard König
Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
published pages: 5162-5166, ISSN: 2041-6520, DOI: 10.1039/c9sc01356c
Chemical Science 10/19 2020-04-24
2019 Martin Jakubec, Indrajit Ghosh, Jan Storch, Burkhard König
Photochemical Functionalization of Helicenes
published pages: 543-547, ISSN: 0947-6539, DOI: 10.1002/chem.201904169
Chemistry – A European Journal 26/2 2020-04-24
2020 Shun Wang, Bei-Yi Cheng, Matea Sršen, Burkhard König
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
published pages: , ISSN: 0002-7863, DOI: 10.1021/jacs.0c00629
Journal of the American Chemical Society 2020-04-24
2020 Tanguy Saget, Burkhard König
Photocatalytic Synthesis of Polycyclic Indolones
published pages: , ISSN: 0947-6539, DOI: 10.1002/chem.202001324
Chemistry - A European Journal 2020-04-24
2020 Joshua P. Barham, Burkhard König
Synthetic Photoelectrochemistry
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201913767
Angewandte Chemie International Edition 2020-04-24
2019 Anna Lucia Berger, Karsten Donabauer, Burkhard König
Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
published pages: 10991-10996, ISSN: 2041-6520, DOI: 10.1039/c9sc04987h
Chemical Science 10/48 2020-04-24
2019 Qing-Yuan Meng, Tobias E. Schirmer, Anna Lucia Berger, Karsten Donabauer, Burkhard König
Photocarboxylation of Benzylic C–H Bonds
published pages: 11393-11397, ISSN: 0002-7863, DOI: 10.1021/jacs.9b05360
Journal of the American Chemical Society 141/29 2020-04-24
2019 Qing-Yuan Meng, Tobias Schirmer, Kousuke Katou, Burkhard König
Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201900849
Angewandte Chemie International Edition 2019-04-18
2019 Veera Reddy Yatham, Peter Bellotti, Burkhard König
Decarboxylative hydrazination of unactivated carboxylic acids by cerium photocatalysis
published pages: 3489-3492, ISSN: 1359-7345, DOI: 10.1039/c9cc00492k
Chemical Communications 55/24 2019-04-18
2019 Shun Wang, Lokesh Nanjundappa, Johnny Hioe, Ruth Maria Gschwind, Burkhard Koenig
Photoinitiated Carbonyl-Metathesis: Deoxygenative Reductive Olefination of Aromatic Aldehydes via Photoredox Catalysis
published pages: , ISSN: 2041-6520, DOI: 10.1039/c9sc00711c
Chemical Science 2019-04-18
2018 Anna Lucia Berger, Karsten Donabauer, Burkhard König
Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones
published pages: 7230-7235, ISSN: 2041-6520, DOI: 10.1039/c8sc02038h
Chemical Science 9/36 2019-04-18

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