Publications associées à NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors of

Divergent Asymmetric Total Synthesis of (−)‐Voacafricines A and B

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres

A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been accomplished featuring the following key steps: a)a catalyst-controlled asymmetric Pictet– Spengler reaction of 6-methoxytryptamine with a ch ...

Wiley-VCH Verlag GmbH2023

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Jocelyn Richard Roth, Wendy Lee Queen, Ilia Kochetygov, Anita Justin, Till Marian Schertenleib, Jordi Espin Marti, Sophia Alessandra Pache, Nazanin Taheri

The design of metal-organic frameworks (MOFs) having large pore sizes and volumes often requires the use of complex organic ligands, currently synthesized using costly and time-consuming palladium-catalyzed coupling chemistry. Thus, in the present work, a ...

Wiley-VCH Verlag GmbH2023

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

Umpolung Of Electron-Rich Heteroarenes With Hypervalent Iodine Reagents

Jérôme Waser, Raj Kumar Nandi

Five-membered heterocycles are well known for their innate nucleophilicity. In contrast, reaction of these heterocycles as electrophiles is less established and has become only recently an intensively investigated research area in synthetic chemistry. The ...

PERGAMON-ELSEVIER SCIENCE LTD2021

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

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

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

Mechanistic Study of the N-Formylation of Amines with Carbon Dioxide and Hydrosilanes

Gabor Laurenczy, Paul Joseph Dyson, Martin Hulla

N-formylation of amines with CO2 and hydrosilane reducing agents proceeds via fast and complex chemical equilibria, which hinder easy analysis of the reaction pathways. In situ reaction monitoring and kinetic studies reveal that three proposed pathways, vi ...

2018

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Pierre Vogel

Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organi ...

2016

Synthesis of Alkynylated Heterocycles by Direct C-H Alkynylation or Domino Alkynylation Reactions

Yifan Li

Heterocycles are important compounds in organic chemistry. To introduce functional groups on heterocycles or synthesize functionalized heterocycles stays a hot topic of research. Among all the functional groups, alkynes attracted a lot of attention not onl ...

EPFL2016

Selenoquinones Stabilized by Ruthenium( II) Arene Complexes: Synthesis, Structure, and Cytotoxicity

Paul Joseph Dyson, Catherine Marie Amélie Clavel

A new series of monoselenoquinone and diselenoquinone complexes, [((6)-p-cymene)Ru((4)-C6R4SeE)] (R=H, E=Se (6); R=CH3, E=Se (7); R=H, E=O (8)), as well as selenolate complexes [((6)-p-cymene)Ru((5)-C6H3R2Se)][SbF6] (R=H (9); R=CH3 (10)), stabilized by are ...

Wiley-V C H Verlag Gmbh2014

Structure and Properties of the Precursor/Successor Complex and Transition State of the CrCl2+/Cr2+ Electron Self-Exchange Reaction via the Inner-Sphere Pathway

François Rotzinger

The electron self-exchange reaction CrCl(OH2)5(2+) + Cr(OH2)6(2+) -> Cr(OH2)(6)(2+) + CrCl(OH2)(5)(2+), proceeding via the inner-sphere pathway, was investigated with quantum-chemical methods. Geometry and vibrational frequencies of the precursor/successor ...

American Chemical Society2014

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

Jieping Zhu, Shuo Tong, Xu Yang

The reactivity of stable tertiary enamides in nucleophilic addition reaction with various in-situ generated imines was explored. Under very mild conditions, formyl-bearing tertiary enamides reacted with both aromatic and aliphatic amines to form imine inte ...

Elsevier2012

The Cause for Tremendous Acceleration of Chloride Substitution via Base Catalysis in the Chloro Pentaammine Cobalt(III) Ion

François Rotzinger, Basile Curchod

The base hydrolysis reaction of Co(NH3)5Cl2+ was investigated using density functional theory and molecular orbital methods. Geometries and energies of conjugate bases, intermediates, transition states, and minimum energy crossing points were computed. For ...

2011

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B-Alkylcatecholboranes

Philippe Renaud, Kurt Schenk

The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The su ...

2010

Wittig rearrangement of lithiated allyl aryl ethers: a mechanistic study

A -75 DegC, alpha-lithiated allyl Ph ether undergoes mainly the Wittig rearrangement to afford, after acidic hydrolysis, 1-phenyl-2-propen-1-ol as the main product. A second metalation taking place at one of the ortho positions is the sole competing side r ...

2006

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

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