Publications related to Position-flexible elaboration of halogenated heterocycles: Metalated species as key intermediates for synthesis

Related publications (20)

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

A Strategy to Conjugate Bioactive Fragments to Cytotoxic Diiron Bis(cyclopentadienyl) Complexes

Paul Joseph Dyson, Mouna Hadiji

A series of bioactive molecules were synthesized from the condensation of aspirin or chlorambucil with terminal alkynes bearing alcohol or amine substituents. Insertion of the resulting alkynes into the iron-carbyne bond of readily accessible diiron bis(cy ...

AMER CHEMICAL SOC2021

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Lionel Schouwey

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first syn ...

2019

Remote C(sp(3))-H Arylation and Vinylation of N-Alkoxypyridinium Salts to delta-Aryl and delta-Vinyl Alcohols

Qian Wang, Jieping Zhu, Xu Bao

The reaction of readily available and bench-stable N-alkoxypyridinium salts with arylboronic and vinylboronic acids afforded delta-aryl and delta-vinyl alcohols, respectively, in the presence of fac-Ir(ppy)(3) and Cu(OTf)(2) dual catalysts. The reaction ta ...

WILEY-V C H VERLAG GMBH2019

Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes

Rosario Scopelliti, Kay Severin, Nicolai Cramer, Gregor Kiefer, Abdusalom Suleymanov, David Kossler, Florian Gérald Abela

Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1-alkynyl triazenes in the presence of a RuII catalyst with a chiral cyclopentadienyl ligand. These triazenes serve as unique vinyl cation surrogates. ...

Wiley-VCH Verlag GmbH2017

On-Surface Assembly and Reactions of Organic Molecules in Ultra-High Vacuum

Claudius Morchutt

This thesis comprises the study of two types of 2D materials, those stabilized by non-covalent and those by covalent interactions. They are synthesized and studied on well-defined metallic surfaces in ultra-high vacuum (UHV). The self-assembly of terephtha ...

EPFL2016

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Jérôme Waser, Paola Caramenti, Maria Victoria Vita

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladiumcatalyzed decarboxylative allylation of alpha-azido and cyano beta-ketoesters is reported. Indano ...

American Chemical Society2015

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

On the Formation and Transformation of alpha-Iminonitriles, the Desymmetrization of Bicyclic Bislactones and Total Synthesis of (-)-Leucomidine B and (-)-Rhazinilam

Jean-Baptiste Gualtierotti

Two principle topics are covered in this thesis. The first section deals with the development of novel synthetically useful multicomponent reactions. The development of three multicomponent reactions, based on α-iminonitriles, is presented. The first descr ...

EPFL2014

Selective in vivo visualization of immune-cell infiltration in a mouse model of autoimmune myocarditis by fluorine-19 cardiac magnetic resonance

Ruud van Heeswijk

Background- The goal of this study was to characterize the performance of fluorine-19 ((19)F) cardiac magnetic resonance (CMR) for the specific detection of inflammatory cells in a mouse model of myocarditis. Intravenously administered perfluorocarbons are ...

2013

Synthesis of C-linked Disaccharides and Analogues as Biomimetics of the TF Epitope

Maria Kolympadi

Glycoproteins and glycolipids are major components of the outer surface of mammalian cells. Their carbohydrate moieties, which are directed into the outer environment, serve as ligands for receptor proteins, such as lectins, pathogen proteins and antibodie ...

EPFL2011

Modulating the Steric, Electronic, and Catalytic Properties of Cp* Ruthenium Half-Sandwich Complexes with β-Diketiminato Ligands

Paul Joseph Dyson, Rosario Scopelliti, Kay Severin, Andrew Douglas Phillips, Katrin Anne Thommes

Five different types of β-diketiminate ligands, bearing electron-donating to strongly electron-withdrawing substituents, were synthesized and used in the synthesis of Cp* ruthenium complexes (Cp* = η5-C5Me5). One series consists of complexes with a covalen ...

American Chemical Society2011

Biologically active secondary metabolites from cyanobacteria

Cyril Portmann

For millennia, nature was the only source of medicine for mankind. Even today natural products represent a large proportion of the drugs in use. In some areas, like cancer or infectious diseases, about 50 % of the compounds used are of natural origin. Cyan ...

EPFL2010

In search of simplicity and flexibility: a rational access to twelve fluoroindolecarboxylic acids

Assunta Ginanneschi

All twelve indolecarboxylic acids carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepd. either directly from the corresponding fluoroindoles or from the chlorinated derivs. by hydrogen/metal permutation ("metalation"), ...

2006

The gas phase acidity of oligofluorobenzenes and oligochlorobenzenes: about the additivity or non-additivity of substituent effects

Fabrice Cottet

The deprotonation energies of benzene, fluorobenzene, all di-, tri-, and tetrafluorobenzenes, pentafluorobenzene, chlorobenzene, all di-, tri-, and tetrachlorobenzenes, and pentachlorobenzene have been calcd. at various levels of second-order Moller-Plesse ...

2005

Fluorine-flanked congested sites: Minimal, though perceptible buttressing effects on the proton mobility of arenes

Christophe Heiss

(2,6-Difluorophenyl)trimethylsilane, -triethylsilane and -triisopropylsilane undergo sec-butyllithium-mediated metalation at the 3- and 4-position (ortho and meta relative to the halogen) in ratios of 99.6:0.4, 98:2 and 95:5, resp. The steric pressure tran ...

2005

The reactivity of 2-fluoro- and 2-chloropyridines toward sodium ethoxide: Factors governing the rates of nucleophilic (het)aromatic substitutions

Thierry Rausis

The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25 Deg were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF3 group increases the ...

2005

Fluorine in an heteroaromatic context : functionalization of halopyridines

Thierry Rausis

The organometallic approach to the functionalization of arenes and heteroarenes has recently been investigated by our group introducing modifications of the standard methods. This includes, in particular, the basicity-driven heavy halogen migration, which ...

EPFL2005

Fate of volatile fluorinated compounds in the subsurface

Christian Balsiger

Since their discovery around 1930, the synthetic compounds of the class of chlorofluorocarbons (CFCs) have been produced and used worldwide at very large scale. Their physico-chemical properties (non-flammability, chemical inertia, miscibility with water a ...

EPFL2004