Synthesis of 4-amino-1,2,3,4-tetrahydropyridine derivatives by intramolecular nucleophilic addition of tertiary enamides to in-situ generated imines

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Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach e ...

2021

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

Diamine Synthesis via the Nitrogen-Directed Azidation of sigma- and pi-C-C Bonds

Jérôme Waser, Mingming Wang

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. ...

2021

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

Jérôme Waser, Mingming Wang

We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the gamma or delta po ...

Wiley-VCH Verlag GmbH2020

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

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

Paul Joseph Dyson, Zhaofu Fei, Xinjiang Cui, Matthias Beller

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

Reactivity and biological activity of N,N,S-Schiff-base rhodium pentamethylcyclopentadienyl complexes

Paul Joseph Dyson, Lucinda Kate Batchelor

Neutral piano-stool complexes of the general formula [(eta(5)-C5Me5)Rh(L-OR)] (R = Me, 1; R = Et, 2; R = Pe(i), 3) have been prepared in alcohols (methanol, 1; ethanol, 2; isopropanol, 3) from the Schiff-base 5-methyl-4-{(pyridin-2-ylmethylene)amino}-4H-1, ...

ELSEVIER SCIENCE SA2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

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

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

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Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

EPFL2020

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

Martin Hulla

EPFL2019

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

Franck Le Vaillant

EPFL2019