Publications associées à Carbon Dioxide Based N-Formylation of Amines Catalyzed by Fluoride and Hydroxide Anions

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

Chlorination of amides: Kinetics and mechanisms of formation of N-chloramides and their reactions with phenolic compounds

Urs von Gunten, Tianqi Zhang

Amides are common constituents in natural organic matter and synthetic chemicals. In this study, we investi-gated kinetics and mechanisms of the reactions of chlorine with seven amides, including acetamide, N-meth-ylformamide, N-methylacetamide, benzamide, ...

2023

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

Shape-controlled Copper Nanocrystals as Electrocatalysts for CO2RR

Pranit Srinivas Iyengar

The electrochemical CO2 reduction reaction (CO2RR) has the potential to mitigate the rising CO2 levels while storing renewable energy in chemical bonds. Copper is the only single metal electrocatalyst producing high energy dense hydrocarbons, albeit into 1 ...

EPFL2021

A polymeric ionic liquid catalyst for the N-formylation and N-methylation of amines using CO2/PhSiH3

Paul Joseph Dyson, Zhaofu Fei, Aswin Gopakumar, Andreas Züttel, Dmitry Vasilyev, Kyriakos Stylianou, Arunraj Chidambaram, Serhii Shyshkanov

We describe a polymeric ionic liquid (PIL) derived from trimethyl(p-vinylbenzyl)ammonium chloride ([VBTAm]Cl) that efficiently catalyzes the N-formylation of amines employing CO2 and PhSiH3 at room temperature with low catalyst loadings in near-quantitativ ...

2020

Acceptorless dehydrogenation and hydrogenation of N- and O-containing compounds on Pd3Au1(111) facets

Paul Joseph Dyson, Zhaofu Fei, Antoine Philippe Van Muyden, Tao Wang, Zhangjun Huang, Xinjiang Cui

Catalytic dehydrogenation and hydrogenation of amines and alcohols are important in the synthesis of fine chemicals. Despite several efficient homogeneous catalysts having been identified, highly active heterogeneous catalysts remain elusive, although they ...

2020

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

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Paul Joseph Dyson, Martin Hulla, Simon Nussbaum, Alexy Robert Bonnin

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...

Royal Society of Chemistry2019

Delineation of the Critical Parameters of Salt Catalysts in the N-Formylation of Amines with CO2

Paul Joseph Dyson, Daniel Ortiz Trujillo, Dmitry Vasilyev, Martin Hulla

N-formylation of amines with CO2 is base-catalyzed and studies of salt catalysts reveal that the reaction is efficiently catalyzed by "free" floating anions of high basicity, as represented in the cover image. More information can be found in the Full Pape ...

WILEY-V C H VERLAG GMBH2019

Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes

Kay Severin, Florian Gérald Abela, Nicolai Cramer, Frederick Mark Chadwick, Jin Fay Tan, Carl Thomas Bormann

Densely substituted fused aromatic triazenes can be prepared by [2 + 2 + 2] cyclotrimerization reactions of 1-alkynyl triazenes. The Cp*Ru-catalyzed cyclization proceeds well with both simple alkynyl triazenes and tethered 1-diynyl triazenes. Attractively, ...

2019

Hydrothermally Stable Sulfonated Carbons as Solid Acid Catalysts for the Hydrolysis of Lignocellulose

David Ferdinand Scholz

The recycling of homogeneous acids imposes great challenges to the feasibility of lignocellulose hydrolysis processes. Although heterogeneous catalysts would offer a perspective to circumvent these challenges, conventional solid acids are instable under th ...

EPFL2019

Molecular engineering of enamine-based small organic compounds as hole-transporting materials for perovskite solar cells

Mohammad Khaja Nazeeruddin, Kyung Taek Cho, Sanghyun Paek, Michael Saliba

The search for new classes of hole transporting materials (HTMs) is a very important task on the way towards commercialization of perovskite solar cells (PSCs). In this work, the synthesis and performance in PSCs of new enamine-based HTMs are presented. Th ...

Royal Society of Chemistry2019

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Development of heterogeneous catalytic systems for the transformation of carbon dioxide to methanol under mild conditions

Aswin Gopakumar

Rising level of carbon dioxide (CO2) is a significant contributor to global warming and poses a major concern in modern society and environment. Anthropogenic activities such as fossil fuel combustion, cement production and deforestation are the primary ca ...

EPFL2018

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

Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production

Jeremy Luterbacher, Christopher Marc Hunston, Masoud Talebi Amiri, Wu Lan

Protection groups were introduced during biomass pretreatment to stabilize lignin's α,γ-diol group during its extraction and prevent its condensation. Acetaldehyde and propionaldehyde stabilized the α,γ-diol without any aromatic ring alkylation, which sign ...

Wiley-VCH Verlag GmbH2018

Decarboxylative C(sp3)–N cross-coupling via synergetic photoredox and copper catalysis

Xile Hu, Adrian Frey, Jonathan Balon, Runze Mao

Amines are a quintessential moiety in bioactive molecules, pharmaceuticals and organic materials. Transition-metal-catalysed C–N coupling of aryl electrophiles has been established as a powerful and reliable method for amine synthesis. However, the analogo ...

2018

High-pressure NMR spectroscopic and calorimetric studies on formic acid dehydrogenation and carbon dioxide hydrogenation

Cornel Fink

Our current energy production is convenient and simple, but it is not sustainable. The negative impacts on our environment are omnipresent in the form of smog, extinction of species, and global warming. A major challenge of our generation is the transition ...

EPFL2018

Hydrogen storage in the carbon dioxide/formic acid system, using homogeneous iron(II)-phosphine catalysts in aqueous solution

Mickael Montandon-Clerc

The valorization of carbon dioxide and its transformation into useful chemicals is essential as mankind consumes more and more fossil fuels, thus producing equivalent wastes. The storage of hydrogen, a promising energy carrier, is also of great interest in ...

EPFL2018