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Related publications (30)

Synthesis of hyperbranched polyarylethenes by consecutive C–H vinylation reactions

Kay Severin, Albert Ruggi, Anastasia Gitlina

A novel procedure for the synthesis of polyarylethenes is described. Consecutive C–H vinylation reactions of tetraphenylethene with a triphenylethenyl triazene give hyperbranched polyarylethenes of variable sizes. The vinylation reactions are mediated by a ...

2023

Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling

Paul Joseph Dyson, Mingyang Liu

Efficient valorization of lignin, a sustainable source of functionalized aromatic products, would reduce dependence on fossil-derived feedstocks. Oxidative depolymerization is frequently applied to lignin to generate phenolic mono- mers. However, due to th ...

Nature Research2023

Photochemical oxidation of phenols and anilines mediated by phenoxyl radicals in aqueous solution

Silvio Canonica, Urs von Gunten, Stephanie Christa Remke

Reactive intermediates formed upon irradiation of chromophoric dissolved organic matter (CDOM) contribute to the degradation of various organic contaminants in surface waters. Besides well-studied "short-lived" photo oxidants, such as triplet state CDOM (3 ...

PERGAMON-ELSEVIER SCIENCE LTD2022

Isolation, Characterisation and Reactivity of N-Heterocyclic Diazoolefins

Paul Varava

Examples for applications of nitrous oxide in organic synthesis remain rare up until today. First mayor contributions of our group were published in 2012, when nitrous oxide was successfully captured by N-heterocyclic carbenes. Subsequent studies investiga ...

EPFL2022

Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst

Jieping Zhu, Qiang Wang, Rémi Julien Sylvain Andres

The asymmetric Pictet–Spengler reaction (PSR) with aldehydes is well known. However, PSR involving ketones as electrophilic partners is far-less developed. We report herein the first examples of catalytic enantioselective PSR of tryptamines with α-ketoamid ...

Wiley-VCH Verlag GmbH2022

Synthetic chemistry with nitrous oxide and triazenes

Iris Roswitha Landman

Nitrous oxide (N2O) has gained much interest because of its physiological effects ("laughing gas") and its negative environmental impact ("greenhouse gas", "ozone-depleting substance"): It has a lifetime of more than 100 years in the atmosphere. Its persis ...

EPFL2022

Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines

Jérôme Waser, Guillaume Dominique Pisella, Nieves Pilar Ramirez Hernandez

The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by a simple Cu(I) salt is described. This three-component reaction allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor ani ...

2021

Engaging 1-Alkynyl Triazenes in Transition Metal-Catalyzed and Fluorinative Transformations

Jin Fay Tan

Triazenes have garnered great attention for their anti-cancer properties and versatility in organic chemistry. Recently, a novel synthesis of 1-alkynyl triazenes was reported. This thesis describes the compatibility, reactivity and applications of 1-alkyny ...

EPFL2021

Learning the Exciton Properties of Azo-dyes

Anne-Clémence Corminboeuf, Alberto Fabrizio, Sergio Vela Llausi, Ksenia Briling

The ab initio determination of electronic excited state (ES) properties is the cornerstone of theoretical photochemistry. Yet, traditional ES methods become impractical when applied to fairly large molecules, or when used on thousands of systems. Machine l ...

AMER CHEMICAL SOC2021

Phototransformation of Organic Contaminants in Aquatic Systems: Characterization of Long-Lived Photooxidants Derived from Dissolved Organic Matter

Stephanie Christa Remke

The increasing interest in the fate of organic contaminants in the aquatic environment requires the elucidation of relevant abiotic transformation processes. These processes often involve the ubiquitous dissolved organic matter (DOM), a complex mixture of ...

EPFL2021

The Photoisomerization Pathway(s) of Push‐Pull Phenylazoheteroarenes

Anne-Clémence Corminboeuf, Sergio Vela Llausi

Azoheteroarenes are the most recent derivatives targeted to further improve the properties of azo‐based photoswitches. Their light‐induced mechanism for trans‐cis isomerization is assumed to be very similar to that of the parent azobenzene. As such, they i ...

2020

Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Kay Severin, Abdusalom Suleymanov

Aromatic compounds containing triazenyl groups (N3RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has change ...

Wiley-VCH Verlag GmbH2021

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Jérôme Waser, Marion Marie-Agnès Garreau, Stephanie Grace Elizabeth Amos, Luca Buzzetti

Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy finetuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this revi ...

2020

Reactions of nitrogen-containing compounds with ozone: kinetics and mechanisms

Sung Eun Lim

Nitrogen-containing moieties are widespread in natural waters in dissolved organic nitrogen and micropollu-tants. They are often susceptible to an electrophilic attack of ozone because of the electron-rich nature of the neutral form of nitrogen in organic ...

EPFL2020

Aliphatic Carboxylic Acids as Coupling Partners in Carbon-Heteroatom Bond-Forming Reactions

Runze Mao

Carboxylic acids are one of the most suitable starting materials for synthesis. They are readily available and therefore inexpensive, stable and non-toxic. Many carboxylic acids can be obtained directly from natural resources, thus avoiding the extraction ...

EPFL2020

Orientation, rotation and solvation of ions in helium nanodroplets

Verónica Oliver Álvarez de Lara

Helium nanodroplets are liquid, finite size, nanoscale helium clusters that have been employed since the 1990s as a matrix for high-resolution spectroscopy of molecules. Spectroscopic studies of ionic species inside helium droplets were not however realise ...

EPFL2019

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Paul Joseph Dyson, Martin Hulla, Simon Nussbaum, Alexy Robert Bonnin

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...

Royal Society of Chemistry2019

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

Investigations of the Chemistry of 1-Alkynyltriazenes

Florian Gérald Abela

The chemistry of aromatic triazenes is well known, and has been explored for more than a century. These compounds have emerged as very useful intermediates, because of their unique reactivity. This functionality can notably be used to access many other fun ...

EPFL2018

Metal-Organic-Framework-Derived Co3S4 Hollow Nanoboxes for the Selective Reduction of Nitroarenes

Safak Bulut, Emad Oveisi, Daniel Teav Sun, Wendy Lee Queen, Li Peng, Shuliang Yang

MOF-derived Co3S4/CN hollow nanoboxes (CN=nitrogen-doped carbon) was used to catalyze the chemoselective reduction of nitroarenes to anilines under mild reaction conditions with H-2 as the reducing agent. The catalyst provides high conversion efficiencies ...

2018

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