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Photons in organic synthesis

English title Photons in organic synthesis
Applicant Bochet Christian
Number 147171
Funding scheme Project funding (Div. I-III)
Research institution Département de Chimie Université de Fribourg
Institution of higher education University of Fribourg - FR
Main discipline Organic Chemistry
Start/End 01.06.2013 - 31.05.2016
Approved amount 423'803.00
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Keywords (2)

photochemistry; organic Synthesis

Lay Summary (French)

Lead
Les plantes sont capables d'utiliser la lumière ainsi que des sources de carbone très bon marché pour assembler des molécules de haute complexité. En revanche, à ce jour, les chimistes n'ont pas vraiment été capables d'imiter ces processus pour la fabrication de substances à usage pharmaceutique. La photochimie, en général, et ce projet en particulier, ont pour but d'étudier ou de mettre au point de nouvelles réactions chimiques capables d'utiliser la lumière comme activateur principal.
Lay summary

La synthèse organique a pour but de fabriquer des molécules à base de carbone. Contrairement à la croyance qu’il est à présent possible de préparer artificiellement n’importe quelle molécule organique, il y a toujours un besoin urgent de nouvelles méthodes d’assemblage de molécules complexes avec un impact sur l’environnement réduit et économiquement viables. Dans cette perspective, la catalyse, en particulier par les métaux de transition et organique, ainsi que la photochimie ont pris un rôle de plus en plus central. L’usage de la lumière en synthèse est particulièrement intéressant pour plusieurs raisons. La lumière est un réactif très propre, qui peut être utilisé en excès sans problème majeur pour l’environnement ; une telle activation des réactifs organiques permet d’assembler des atomes de manière inédite, souvent complémentaire aux méthodes classiques ; la lumière est une espèce relativement bon marché, et surtout disponible en abondance via le soleil. Ce projet a pour but d’étudier a) l’usage de la lumière dans de nouvelles réactions dites de « photocyloaddition », b) la libération d’espèces actives à l’aide de la lumière, et c) de former des liaisons peptidiques par activation lumineuse.

Direct link to Lay Summary Last update: 02.04.2013

Responsible applicant and co-applicants

Employees

Publications

Publication
Arene-Alkene Cycloaddition.
Remy Richard, Bochet Christian G (2016), Arene-Alkene Cycloaddition., in Chemical reviews, .(.), .-..
Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.
Chetioui Souheyla, Rouag Djamil-Azzeddine, Djukic Jean-Pierre, Bochet Christian G, Touzani Rachid, Bailly Corinne, Crochet Aurélien, Fromm Katharina M (2016), Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol., in Acta crystallographica. Section E, Crystallographic communications, 72(Pt 8), 1093-8.
Probing Mechanisms of Photochemical Reactions: How to Teach a Young Dog Old Tricks.
Bochet Christian G (2016), Probing Mechanisms of Photochemical Reactions: How to Teach a Young Dog Old Tricks., in Chimia, 70(3), 182-5.
Supramolecular Agent--Simulant Correlations for the Luminescence Based Detection of V‐Series Chemical Warfare Agents with Trivalent Lanthanide Complexes
Dennison G H, Bochet C G, Curty C (2016), Supramolecular Agent--Simulant Correlations for the Luminescence Based Detection of V‐Series Chemical Warfare Agents with Trivalent Lanthanide Complexes, in European Journal of Inorganic Chemistry, ..
Crystal structure of bis-{μ-1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(3) N (2),O:O}bis-({1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(2) N (2),O}copper(II)).
Chetioui Souheyla, Hamdouni Noudjoud, Bochet Christian G, Djukic Jean-Pierre, Bailly Corinne (2015), Crystal structure of bis-{μ-1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(3) N (2),O:O}bis-({1-[(E)-(3-meth-oxy-phen-yl)diazen-yl]naphthalen-2-olato-κ(2) N (2),O}copper(II))., in Acta crystallographica. Section E, Crystallographic communications, 71(Pt 12), 211-2.
Cytotoxic flavonoids and other constituents from the stem bark of Ochna schweinfurthiana
Ndongo J T, Issa M E, Messi A N, Mbing J Ngo (2015), Cytotoxic flavonoids and other constituents from the stem bark of Ochna schweinfurthiana, in Natural product research, 1684-1687.
Reply to Commentary by Trentham et al. on "Caged Phosphate and the Slips and Misses in Determination of Quantum Yields for Ultraviolet-A-Induced Photouncaging" by Gasser et al.
Anstaett Philipp, Leonidova Anna, Janett Elia, Bochet Christian G, Gasser Gilles (2015), Reply to Commentary by Trentham et al. on "Caged Phosphate and the Slips and Misses in Determination of Quantum Yields for Ultraviolet-A-Induced Photouncaging" by Gasser et al., in Chemphyschem : a European journal of chemical physics and physical chemistry, 16(9), 1863-6.
Synthesis of FMRFaNV, a Photoreleasable Caged Transmitter Designed to Study Neuron-Glia Interactions in the Central Nervous System.
Janett Elia, Bernardinelli Yann, Müller Dominique, Bochet Christian G (2015), Synthesis of FMRFaNV, a Photoreleasable Caged Transmitter Designed to Study Neuron-Glia Interactions in the Central Nervous System., in Bioconjugate chemistry, 26(12), 2408-18.
Activity-Dependent Structural Plasticity of Perisynaptic Astrocytic Domains Promotes Excitatory Synapse Stability
Bernardinelli Yann, Randall Jerome, Janett Elia, Nikonenko Irina, König St{é}phane, Jones Emma Victoria, Flores Carmen E, Murai Keith K, Bochet Christian G, Holtmaat Anthony, Muller Dominique (2014), Activity-Dependent Structural Plasticity of Perisynaptic Astrocytic Domains Promotes Excitatory Synapse Stability, in Current Biology, 24(15), 1679-1688.
Activity-dependent structural plasticity of perisynaptic astrocytic domains promotes excitatory synapse stability.
Bernardinelli Yann, Randall Jerome, Janett Elia, Nikonenko Irina, König Stéphane, Jones Emma Victoria, Flores Carmen E, Murai Keith K, Bochet Christian G, Holtmaat Anthony, Muller Dominique (2014), Activity-dependent structural plasticity of perisynaptic astrocytic domains promotes excitatory synapse stability., in Current biology : CB, 24(15), 1679-88.
Cell-Permeant and Photocleavable Chemical Inducer of Dimerization
Zimmermann Mirjam, Cal Ruben, Janett Elia, Hoffmann Viktor, Bochet Christian G, Constable Edwin, Beaufils Florent, Wymann Matthias P (2014), Cell-Permeant and Photocleavable Chemical Inducer of Dimerization, in Angewandte Chemie International Edition, 53(18), 4717-4720.
Photocycloaddition of arenes and allenes.
Streit Ursula, Birbaum Frédéric, Quattropani Anna, Bochet Christian G (2013), Photocycloaddition of arenes and allenes., in The Journal of organic chemistry, 78(14), 6890-910.
Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.
Kl{á}n Petr, {\v S}olomek Tom{á}{\v s}, Bochet Christian G, Blanc Aur{é}lien, Givens Richard, Rubina Marina, Popik Vladimir, Kostikov Alexey, Wirz Jakob (2013), Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy., in Chemical Reviews, 113(1), 119-191.
The primary steps in excited-state hydrogen transfer: the phototautomerization of o-nitrobenzyl derivatives.
Šolomek Tomáš, Bochet Christian G, Bally Thomas (2013), The primary steps in excited-state hydrogen transfer: the phototautomerization of o-nitrobenzyl derivatives., in Chemistry (Weinheim an der Bergstrasse, Germany), 20(26), 8062-7.
Towards a photochemical synthesis of peptides.
Bochet Christian G (2013), Towards a photochemical synthesis of peptides., in Chimia, 67(12-13), 896-8.

Associated projects

Number Title Start Funding scheme
129617 Photons in organic synthesis 01.06.2010 Project funding (Div. I-III)
165856 Photons in organic synthesis 01.06.2016 Project funding (Div. I-III)

Abstract

Organic synthesis is the science aiming at preparing carbon-containing substances. Despite the popular belief that it is now possible to prepare any organic molecule, organic synthesis is still in an urgent need of significant advances, for a more efficient assembly of complex structures, a cleaner environmental footprint, and more cost effective. As a consequence, organometallic chemistry and transition-metal catalysis, organocatalysis and photochemistry have seen a recent increase in research activity. The use of light in synthesis is particularly appealing for many reasons: light is a very clean reagent, for which the unused excess can be freely released without significant harm, and it allows the construction of complex structures in a very rapid way. In this project, we will study a) the use of light in new photocycloadditions, b) develop new tools for the photorelease of active substances, and c) exploit and improve peptide bond-forming photoprocesses.
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