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Photons in organic synthesis

English title Photons in organic synthesis
Applicant Bochet Christian
Number 129617
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 01.06.2010 - 31.05.2013
Approved amount 412'973.00
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Keywords (4)

organic Synthesis; photochemistry; Chemistry; Combinatorial chemistry

Lay Summary (French)

Lead
Lay summary
Les techniques récentes de synthèse de molécules organique permettent de créer rapidement des collections de composés destinés à l'évaluation biologique ("high-throughput screening"). Par contre, l'usage de la lumière n'a pas encore été exploité dans ce cadre, malgré sa simplicité expérimentale, son faible coût et l'absence de réactifs dangereux pour l'environnement. Ce projet a pour but d'intégrer des transformations photochimique simultanément sur l'ensemble des membres d'une collection de composés. En parallèle, les mécanismes fondamentaux de réactions photochimiques seront étudiés, en particulier à l'aide de l'isotope lourd de l'hydrogène, le deutérium. L'usage de rayons laser focalisés est prévu pour provoquer l'absorption simultanée de plusieurs particules de lumière (excitation multi-photons).
Direct link to Lay Summary Last update: 21.02.2013

Responsible applicant and co-applicants

Employees

Publications

Publication
Towards a photochemical synthesis of peptides
Bochet C. G. (2014), Towards a photochemical synthesis of peptides, in Chimia, 67, 896-898.
Ethyl 5-meth-oxy-2-trifluoro-methyl-1H-indole-3-carboxyl-ate.
Crochet Aurelien, Alimi Isak, Bochet Christian G, Fromm Katharina M (2013), Ethyl 5-meth-oxy-2-trifluoro-methyl-1H-indole-3-carboxyl-ate., in Acta crystallographica. Section E, Structure reports online, 69(Pt 3), 339-339.
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.
Klán Petr, Šolomek Tomáš, Bochet Christian G, Blanc Aurélien, 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), 119-91.
Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group.
Solomek Tomáš, Mercier Sébastien, Bally Thomas, Bochet Christian G (2012), Photolysis of ortho-nitrobenzylic derivatives: the importance of the leaving group., in Photochemical & photobiological sciences : Official journal of the European Photochemistry Associati, 11(3), 548-55.
The all-photochemical synthesis of an OGP(10-14) precursor
Débieux J. L., Bochet C. G. (2012), The all-photochemical synthesis of an OGP(10-14) precursor, in Chem. Sci., 3, 405-406.
41th CUSO Summer School in Organic Chemistry, 29.8-2.9.2010. 'Unconventional methods in organic synthesis'.
Jack Thomas, Simonin Jonathan, Singhanat Suradech, Bochet Christian G (2011), 41th CUSO Summer School in Organic Chemistry, 29.8-2.9.2010. 'Unconventional methods in organic synthesis'., in Chimia, 65(1-2), 97-9.
Photolabile protecting groups in organic synthesis
Blanc A., Bochet C. G. (2011), Photolabile protecting groups in organic synthesis, in Griesbeck A., Oelgemoeller M. (ed.), Taylor and Francis, New York, 1.
Singlet oxygen-induced rearrangement of furan derivatives
Charbonnet N., Riguet E., Bochet C. G. (2011), Singlet oxygen-induced rearrangement of furan derivatives, in Synlett, 2011, 2231-2233.
The arene-alkene photocycloaddition.
Streit Ursula, Bochet Christian G (2011), The arene-alkene photocycloaddition., in Beilstein journal of organic chemistry, 7, 525-42.
Total synthesis of the Amaryllidaceae alkaloid clivonine.
Haning Helmut, Giró-Mañas Carles, Paddock Victoria L, Bochet Christian G, White Andrew J P, Bernardinelli Gerald, Mann Inderjit, Oppolzer Wolfang, Spivey Alan C (2011), Total synthesis of the Amaryllidaceae alkaloid clivonine., in Organic & biomolecular chemistry, 9(8), 2809-20.
Wavelength-selective caged surfaces: how many functional levels are possible?
San Miguel Verónica, Bochet Christian G, del Campo Aránzazu (2011), Wavelength-selective caged surfaces: how many functional levels are possible?, in Journal of the American Chemical Society, 133(14), 5380-8.
Photoinduced acyl transfer
Débieux J. L., Bochet C. G. (2010), Photoinduced acyl transfer, in J. Phys. Org. Chem., 23, 272-282.
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.
Giró Mañas Carles, Paddock Victoria L, Bochet Christian G, Spivey Alan C, White Andrew J P, Mann Inderjit, Oppolzer Wolfgang (2010), Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor., in Journal of the American Chemical Society, 132(14), 5176-8.
Cell Permeant and Photocleavable Chemical Inducer of Dimerization
Zimmermann M., Cal R., Janett E., Hoffmann V., Bochet C.G., Constable E., Beaufils F., Wymann M. P., Cell Permeant and Photocleavable Chemical Inducer of Dimerization, in Angew. Chem. Int. Ed., 2014.
Organic Photochemistry
Bochet C. G., Organic Photochemistry, in Welch C., Knochel P, Molander G. (ed.), Elsevier, x.
The Primary Steps in Excited State Hydrogen Transfer: The Phototautomerization of o-Nitrobenzyl Derivatives
Solomek Tomas, Bochet Christian G., Bally T, The Primary Steps in Excited State Hydrogen Transfer: The Phototautomerization of o-Nitrobenzyl Derivatives, in Chem. Eur. J., 2014.

Associated projects

Number Title Start Funding scheme
117740 Asymmetric organocatalysis in photochemistry 01.06.2008 Project funding (Div. I-III)
147171 Photons in organic synthesis 01.06.2013 Project funding (Div. I-III)
112709 Selective photochemical control of organic reactions 01.11.2006 SNSF Professorships
117740 Asymmetric organocatalysis in photochemistry 01.06.2008 Project funding (Div. I-III)

Abstract

We intend to expand the scope of combinatorial libraries by post-condensation transformations, in particular using photochemistry, because of its very simple experimental setup, and possibility of affecting the whole library in one step. In parallel, we will continue our ongoing investigation on the exact mechanism of photolysis of ortho-nitrobenzylic esters or ethers, using to use the kinetic isotope effect as an unconventional tool for probing photochemical reactions. Finally, we intent to identify existing or develop new photosensitive groups which exhibit mutual chromatic orthogonality, not (as we have shown in earlier work) between different wavelengths, but rather between one vs two-photon excitation using focused or defocused laser beams.
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