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Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

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Publications associées (36)

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Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

Jérôme Waser, Stefano Nicolai, Stephanie Grace Elizabeth Amos

We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolu ...

2020

Development of Photocatalysts towards the Visible-Light driven C-Terminal Bioconjugation of Peptides and Proteins

Marion Marie-Agnès Garreau

If small molecules have led to tremendous progress in curing diseases, new therapeutic agents such as peptides or antibody-drugs conjugates have emerged as a highly promising next generation of pharmaceuticals. As for small molecules, their derivatization ...

EPFL2020

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core-Shell Cobalt Nanoparticles

Paul Joseph Dyson, Zhaofu Fei, Xinjiang Cui

Core-shell nanocatalysts are attractive due to their versatility and stability. Here, we describe cobalt nanoparticles encapsulated within graphitic shells prepared via the pyrolysis of a cationic poly-ionic liquid (PIL) with a cobalt(II) chloride anion. T ...

Wiley-VCH Verlag GmbH2020

Acceptorless dehydrogenation and hydrogenation of N- and O-containing compounds on Pd3Au1(111) facets

Paul Joseph Dyson, Zhaofu Fei, Antoine Philippe Van Muyden, Zhangjun Huang, Xinjiang Cui

Catalytic dehydrogenation and hydrogenation of amines and alcohols are important in the synthesis of fine chemicals. Despite several efficient homogeneous catalysts having been identified, highly active heterogeneous catalysts remain elusive, although they ...

2020

Dyes, Radicals and Nitrous Oxide Adducts Derived from N-Heterocyclic Carbenes

Léonard Yannick Maurice Eymann

N-Heterocyclic carbenes are able to form covalent adducts with nitrous oxide (N2O) under ambient conditions. This thesis summarizes the studies of these adducts and their reactivity. A ditopic carbanionic N-heterocyclic carbene was found to react with nit ...

EPFL2018

Iron-Catalyzed Reductive Coupling of Alkyl Iodides with Alkynes To Yield cis-Olefins: Mechanistic Insights from Computation

Xile Hu

In a recent study, a new procedure for Z-selective olefin synthesis by reductive coupling of alkyl iodides with terminal alkynes in the presence of iron salts is described. This transformation is representative of many newly developed synthetic routes thro ...

AMER CHEMICAL SOC2020

Suitability of Cu-substituted beta-Mn2V2O7 and Mn-substituted beta-Cu2V2O7 for photocatalytic water-splitting

Raffaella Buonsanti, Michal Stanislaw Strach

The pyrovanadates beta -Mn2V2O7 and beta -Cu2V2O7 were previously investigated as photoanode materials for water splitting. Neither of them, however, was found to be sufficiently active. In this work, we predict the properties of these two structurally sim ...

AMER INST PHYSICS2020

Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

Shyamal Chakrabarty, Jérôme Waser, Johannes Preindl

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...

2017

Photoredox-Catalyzed Decarboxylation for the Transfer of Alkynes and Nitriles Using Hypervalent Iodine Reagents

Franck Le Vaillant

Aliphatic alkynes and nitriles are privileged motifs in organic chemistry. Therefore, alkynes and nitriles have played a central role for the exploration and development of novel strategies to forge C-C bonds in efficient manner. They are broadly used as v ...

EPFL2019

Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition

Xile Hu, Guido Barzanò, Alexis Baptiste Cheseaux

Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stere ...

2019

Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents

Jérôme Waser, Franck Le Vaillant

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild cond ...

2017

Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds

Jérôme Waser, Franck Le Vaillant

The alkynylation of radical intermediates has been known since a long time, but had not been broadly applied in synthetic chemistry, in contrast to the alkynylation of either electrophiles or nucleophiles. In the last decade however, it has been intensivel ...

2019

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

Jérôme Waser, Matthew Wodrich, Franck Le Vaillant

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and no ...

2017

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2

Martin Hulla

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

EPFL2019

In Situ Tethering Strategies for the 3-Component Synthesis of Vicinal Amino Alcohols and Diamines via Pd-Catalyzed Carboetherification and Carboamination

Ugo Jonathan Orcel

Vicinal amino alcohols and diamines are privileged motifs in organic chemistry. As such, they have been targets of choice for exploring and developing novel and more efficient strategies in organic synthesis. In this context, the difunctionalization of ole ...

EPFL2017

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Fedor Zhurkin

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017