Publications related to Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Related publications (17)

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

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

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

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

Getting the Right Grip? How Understanding Electrophile Selectivity Profiles Could Illuminate Our Understanding of Redox Signaling

Yimon Aye, Lingxi Wang

Recent Advances: Herein, we focus on the first step of this process, electrophile sensing. Electrophile sensing is typically a deceptively simple reaction between the thiol of a protein cysteine, of which there are around 200,000 in the human proteome, and ...

MARY ANN LIEBERT, INC2020

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

Insights into Reaction Intermediates to Predict Synthetic Pathways for Shape-Controlled Metal Nanocrystals

Anne-Clémence Corminboeuf, Raffaella Buonsanti, Anna Loiudice, Shubhajit Das, James Richard Pankhurst, Valeria Mantella, Pranit Srinivas Iyengar, Michal Stanislaw Strach

Understanding nucleation phenomena is crucial across all branches of physical and natural sciences. Colloidal nanocrystals are among the most versatile and tunable synthetic nanomaterials. While huge steps have been made in their synthetic development, syn ...

2019

Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence

Jieping Zhu, Qian Wang, Shuo Tong

Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom syntho ...

Wiley-Blackwell2016

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

Real Time Determination of the Electronic Structure of Unstable Reaction Intermediates during Au2O3 Reduction

Chemical reactions are always associated with electronic structure changes of the involved chemical species. Determining the electronic configuration of an atom allows probing its chemical state and gives understanding of the reaction pathways. However, of ...

Amer Chemical Soc2014

Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism

Jérôme Waser, Matthew Wodrich, Reto Frei, Durga Prasada Rao Hari

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with ...

2014

Influence of Halogen Atoms on a Homologous Series of Bis-Cyclometalated Iridium(III) Complexes

Michael Graetzel, Mohammad Khaja Nazeeruddin, Rosario Scopelliti, Ursula Röthlisberger, Ivano Tavernelli, Basile Curchod

A series of homologous bis-cyclometalated iridium(III) complexes Ir(2,4-di-X-phenyl-pyridine)2(picolinate) (X = H, F, Cl, Br) HIrPic, FIrPic, ClIrPic, and BrIrPic has been synthesized and characterized by NMR, X-ray crystallography, UV–vis absorption and e ...

2012

Unraveling the Catalytic Pathway of Metalloenzyme Farnesyltransferase through QM/MM Computation

Matteo Dal Peraro

The protein farnesyltransferase (FTase) is a Zn2+-metalloenzyme that catalyzes the farnesylation reaction, i.e., the transfer of the 15-carbon atom farnesyl group from farnesyl diphosphate (FPP) to a specific cysteine of protein substrates. Oncogenic Ras p ...

2009

Fluorinated β-Diketones for the Extraction of Lanthanide Ions: Photophysical Properties and Hydration Numbers of Their EuIII Complexes

Jean-Claude Bünzli, Anne-Sophie Chauvin, Frédéric Gumy

Tris(β-diketonato)europium(III) with a series of variably fluorinated ligands derived from 3,5-heptanedione were synthesised with the aim of determining their hydration state under extraction conditions. The number of coordinated water molecules was determ ...

2006

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

Removal of fluorine from and introduction of fluorine into polyhalopyridines: an exercise in nucleophilic hetarenic substitution

Carla Bobbio, Thierry Rausis

Starting from six industrially available fluorinated pyridines, an expedient access to all three tetrafluoropyridines, all six trifluoropyridines, and the five non-com. difluoropyridines was developed. The methods employed for the selective removal of fluo ...

2005

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

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