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Fluorophenols and (trifluoromethyl)phenols as substrates of site-selective metalation reactions: to protect or not to protect

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Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ...

EPFL2023

Synthetic Studies toward Amanita Phalloides Toxins

Philipp Georg Werner Seeberger

Amatoxins are ribosomally synthesized and post-translationally modified bicyclic octapeptides biosynthesized by the deadly basidiomycete fungus Amanita phalloides. Amongst this group, alpha-amanitin is the most widely known toxin and is currently under inv ...

EPFL2020

Ozonation of Para-Substituted Phenolic Compounds Yields p-Benzoquinones, Other Cyclic α,β-Unsaturated Ketones, and Substituted Catechols

Urs von Gunten, Peter Rudolf Tentscher

Phenolic moieties are common functional groups in organic micropollutants and in dissolved organic matter, and are exposed to ozone during drinking water and wastewater ozonation. Although unsubstituted phenol is known to yield potentially genotoxic p-benz ...

2018

Total Synthesis of Alstilobanine C, Undulifoline and Alstilobanine B

Nicolas David Gaeng

The total synthesis of pentacyclic monoterpene indole alkaloids is the focus of this thesis. Total syntheses of (±)-alstilobanine C, (±)-undulifoline and (±)-alstilobanine B, three natural products from the Ulean family of alkaloids, were accomplished. The ...

EPFL2018

On-surface transmetalation of metalloporphyrins

Klaus Kern, Jan Gui-Hyon Dreiser, Pietro Gambardella, Markus Etzkorn, Claudius Morchutt, Sebastian Stepanow, Patrick Eduard Alexa

Increasing the complexity of 2D metal-organic networks has led to the fabrication of structures with interesting magnetic and catalytic properties. However, increasing complexity by providing different coordination environments for different metal types im ...

2018

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

Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts - Electrophilic aromatic substitution and oxidation

Urs von Gunten, Eva Maria Rodriguez Franco

Phenolic compounds are known structural moieties of natural organic matter (NOM), and their reactivity is a key parameter for understanding the reactivity of NOM and the disinfection by-product formation during oxidative water treatment. In this study, spe ...

Elsevier2015

Substituent effects on the relative rates and free energies of ortho-lithiation reactions: families of fluorobenzenes as the substrates

2-, 3- and 4-substituted fluorobenzenes and 5-substituted 1,3-difluorobenzenes were metalated with sec-butyllithium (LIS) and with lithium 2,2,6,6-tetramethylpiperidide (LiTMP) under irreversible conditions in order to determine the rates of reaction relat ...

Arkat Usa Inc2015

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates

Jérôme Waser, Jonathan Brand, Davinia Fernández González

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scanning ...

Wiley-Blackwell2013

Development of Catalytic Umpolung

Jonathan Brand

The development of efficient synthetic methodologies is crucial to access complex molecules in an economic, eco-friendly and safe way. The reversal of the intrinsic reactivity of functional groups, called Umpolung, allows alternative synthetic strategies a ...

EPFL2012