Publications related to Around isocyanide reactivity : development of enantioselective transformations and syntheses of heterocycles and natural products

CO2 Capture and Release in Amine Solutions: To What Extent Can Molecular Simulations Help Understand the Trends?

Wanda Andreoni, Fabio Pietrucci, Changru Ma

Absorption in amine solutions is a well-established advanced technology for CO2 capture. However, the fundamental aspects of the chemical reactions occurring in solution still appear to be unclear. Our previous investigation of aqueous monoethanolamine (ME ...

2023

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

Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Jieping Zhu, Shuo Tong

We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derive ...

2020

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

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

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

Chemoselective three-phase hydrogenation of an Ombrabulin nitro-stilbene intermediate in a continuous-flow mobile platform

Lioubov Kiwi, Charline Berguerand

The chemoselective three-phase hydrogenation of an Ombrabulinintermediate based on a nitro-stilbene framework was used as a case study for the formation of the primary amine without affecting the double bond. Two catalysts were tested: Pt nanoparticles sup ...

Elsevier Science Sa2017

Dearomatization of electron poor six-membered N-heterocycles through [3+2] annulation with aminocyclopropanes

Jérôme Waser, Shyamal Chakrabarty, Johannes Preindl

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor- ...

2017

α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity

Qian Wang, Jieping Zhu, Mathias Mamboury

The palladium-catalyzed reaction of a-haloketones with isocyanides afforded -oxo-ketenimines through alpha-hydride elimination of the beta-oxo-imidoyl palladium intermediates. Reaction of these relatively stable alpha-oxo ketenimines with nucleophiles suc ...

Wiley-Blackwell2017

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

Qian Wang, Jieping Zhu, 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

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

Total Synthesis of (±)-Strictamine

Qian Wang, Jieping Zhu, Weiwu Ren

The total synthesis of strictamine has been achieved in nine steps from a known enol triflate. Characteristic features of our approach included: a) creation of a C7 all-carbon quaternary stereocenter at an early synthetic stage; b) use of an N,N-dimethyl t ...

Wiley-Blackwell2016

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

Paul Joseph Dyson, Felix Daniel Bobbink, Shoubhik Das, Martin Hulla

We described herein a simple approach for N-formylation with CO2 and hydrosilane reducing agents. Fluoride and hydroxide salts efficiently catalyzed the reaction, principally through activation of the hydrosilanes, which led to hydrosilane reactivities com ...

Wiley-VCH Verlag2016

Tuning the Reactivity of Isocyano Group: Synthesis of Imidazoles and Imidazoliums from Propargylamines and Isonitriles in the Presence of Multiple Catalysts

Qian Wang, Jieping Zhu, Shuo Tong

The reaction of propargyl amines with tert-butylisonitrile in the presence of a catalytic amount of both Yb(OTf)3 and AgOTf afforded imidazoles, whereas the same reaction with primary and secondary alkylisonitriles, as well as arylisonitriles, in the prese ...

Wiley-Blackwell2015

Rational Catalyst Design for Selective Hydrogenations : Nitroarenes and Alkynes as Case Studies

Daniel André Samuel Lamey

Catalyst design for selective hydrogenations is of major importance for the manufacturing of fine chemicals. Catalytic procedure which uses scarce and expensive noble metals is very challenging in terms of exclusive attack of a single functionality or subs ...

EPFL2015

New Acetylene Chemistry : Direct [alpha]-Alkynylation of Carbonyls with Ethynyl Benziodoxolones (EBX)

Davinia Fernández González

This thesis is divided in seven main chapters including an introduction about the state of the art in the field, four main chapters describing the main part of the work, a short insight on the implications of the presented results for other research projec ...

EPFL2011