Publications associées à Silylium-Catalyzed Activation of DonorAcceptor Strained Rings and Annulation with Indoles

Publications associées (18)

Development of synthetic methods starting from cyclopropenes: taming cyclopropyl radical, cyclopropyl and cyclopropenium cations

Due to the high ring strain and unique bonding, cyclopropenes represent important 3-carbon synthons in organic synthesis. Intrigued by the unique reactivity of cyclopropenes, we were interested in further exploration of their chemical properties. Trying to ...

EPFL2025

Radical-Mediated Azidation of Benzylic C-H Bonds and Azidofunctionalization of Alkenes

Pierre Gérard Joseph Palamini

Organic azides are known for their reactivity and broad applicability in organic synthesis. These compounds are pivotal in various chemical transformations, including nucleophilic substitution and cycloaddition reactions. Beyond synthetic chemistry, organi ...

EPFL2025

New Applications of 1,3,2-Diazaphospholenes in Catalysis

Johannes Klett

The constant urge to construct new molecules in an economical and sustainable fashion led to the development of numerous metal-catalyzed transformations. Organocatalysts consisting of abundant and more sustainable elements offer an elegant solution to over ...

EPFL2024

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

Donor-Acceptor Aminocyclobutane Monoesters: Synthesis and Silylium-Catalyzed (4+2) Annulation with Indoles

Jérôme Waser, Matthew Wodrich, Emma Gabrielle Louise Robert, Vincent Géry C Pirenne

A convenient one-step synthesis of beta-aminocyclobutane monoesters starting from commercially available reagents is reported. The obtained strained rings undergo (4+2) dearomative annulation with indole partners using silylium catalysis. This organocataly ...

Wiley-VCH Verlag GmbH2023

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Oleksandr Liashuk, Jérôme Waser

A photochemical [2+2] cycloaddition of alkynyl boronates and maleimides is reported. The developed protocol provided 35–70 % yield of maleimide-derived cyclobutenyl boronates and demonstrated wide compatibility with various functional groups. The synthetic ...

2023

Isolation, Characterisation and Reactivity of N-Heterocyclic Diazoolefins

Paul Varava

Examples for applications of nitrous oxide in organic synthesis remain rare up until today. First mayor contributions of our group were published in 2012, when nitrous oxide was successfully captured by N-heterocyclic carbenes. Subsequent studies investiga ...

EPFL2022

Catalytic Enantioselective Synthesis of Morpholinones Enabled by Aza-Benzilic Ester Rearrangement

Jieping Zhu, Qian Wang, Hua Wu

Chiral morpholinone is an important building block in organic synthesis and a pharmacophore in medicinal chemistry. However, catalytic enantioselective methods for the construction of this N,O-heterocycle remain scarce. We report herein a chiral phosphoric ...

2021

1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids

Nicolai Cramer, John Henry Reed

The potent nucleophilicity and remarkably low basicity of 1,3,2- diazaphospholenes (DAPs) is exploited in a catalytic, metal-free 1,4-reduction of free ,-unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the car ...

Wiley-VCH Verlag2020

Advances in heterogeneous catalysis for the synthesis of polyoxymethylene dimethyl ethers

Christophe Jean Baranowski

Our society is engaged in a major shift towards more sustainable industries. The required transition from fossils to renewable resources with low greenhouse gas emission is specifically challenging in the transportation sector where high thermal efficiency ...

EPFL2020

Nickamine and Analogous Nickel Pincer Catalysts for Cross-Coupling of Alkyl Halides and Hydrosilylation of Alkenes

Xile Hu, Zhikun Zhang, Renyi Shi

CONSPECTUS: Ligand development plays an essential role in the advance of homogeneous catalysis. Tridentate, meridionally coordinating ligands, commonly termed pincer ligands, have been established as a privileged class of ligands in catalysis because they ...

American Chemical Society2019

Deoxygenative trifluoromethylthiolation of carboxylic acids

Xile Hu, Runze Mao, Srikrishna Bera, Alexis Baptiste Cheseaux

Here we describe a deoxygenative trifluoromethylthiolation method that yields trifluoromethyl thioesters from readily available carboxylic acids. The method is built upon an "umpolung" strategy where triphenylphosphine is used to first activate an electrop ...

2019

Catalytic valorization of the acetate fraction of biomass to aromatics and its integration into the carboxylate platform

Jeremy Luterbacher, Benjamin Pierre Le Monnier, Masoud Talebi Amiri, Ydna Marie Questell-Santiago, Jher Hau Yeap, Bartosz Rozmyslowicz

In many plant species, the acetate fraction is the fourth most prominent fraction by weight after cellulose, hemicellulose and lignin, and can be easily extracted as a single stable molecule, acetic acid, at high yields. Despite this, upgrading the acetate ...

2019

Design of Surface-Supported Bio-inspired Networks for CO2 and O2 Activation at Room Temperature

Daniel Eduardo Hurtado Salinas

The structure of a biological system defines its function. Therefore, nature has developed sophisticated systems that catalyze chemical reactions that are vital for life on earth. For instance, the photosynthesis is a biological process that is partially r ...

EPFL2018

Organocatalytic Nucleophilic Addition of Hydrazones to Imines: Synthesis of Enantioenriched Vicinal Diamines

Jieping Zhu, Qian Wang, Yang Wang

In the presence of a catalytic amount of chiral phosphoric acid, nucleophilic addition of N-monosubstituted hydrazones to N-Boc imines affords differentially protected vicinal diamines in the form of b-amino N,N’-dialkyldiazenes in excellent yields with hi ...

Wiley-Blackwell2017

Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates

Jieping Zhu, Qian Wang, Yang Wang

The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinolinefused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields ...

Wiley-Blackwell2016

Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application

Jieping Zhu

Tandem reactions for the efficient synthesis of multifunctionalized 1,2,3,4-tetrahydropyridines, 2,3-dihydropyridin-4(1H)-ones, and pyridine derivatives have been developed and reaction mechanisms have been investigated. Synthetic cascades are initiated by ...

Wiley-Blackwell2013