Publications associées à Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

Publications associées (32)

Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts

The alkyne motif is a versatile functional group often encountered in organic chemistry. It can be involved in various transformations such as the alkyne-azide cycloaddition and has found widespread application in medicinal chemistry, chemical biology and ...

EPFL2024

Development of Hetero-Vinylbenziodoxolone Reagents for Applications in Synthetic Methodology and Biomolecule Functionalization

Nina Declas

Among the numerous existing chemical motifs, alkenes, alkynes, enol ethers and enamides, with an unsaturated carbon-carbon bond, are versatile functional groups that are found in many natural products and bioactive compounds. They are widely used as valuab ...

EPFL2023

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Rémi Hugo Lavernhe

The first chapter of this thesis describe the development of a general synthesis of ynimines, an under-exploited motif in organic chemistry. In the presence of an inexpensive copper catalyst and 2,2'-biquinoline, reaction of easily accessible O-acyloximes ...

EPFL2023

Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction

Jérôme Waser, Mikus Purins, Lucas Antoine Théo Eichenberger

Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-se ...

Royal Society of Chemistry2023

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

Synthesis of hyperbranched polyarylethenes by consecutive C–H vinylation reactions

Kay Severin, Albert Ruggi, Anastasia Gitlina

A novel procedure for the synthesis of polyarylethenes is described. Consecutive C–H vinylation reactions of tetraphenylethene with a triphenylethenyl triazene give hyperbranched polyarylethenes of variable sizes. The vinylation reactions are mediated by a ...

2023

Oxidative rearrangement of 1,1-disubstituted alkenes to ketones

Qian Wang, Jieping Zhu, Qiang Feng

The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a PdII/Pd0 catalytic cycle involving a b-hydride elimination step. This mechanistic scenario is inapplicable to ...

American Association for the Advancement of Science2023

Synthesis and application of bifunctional hypervalent iodine reagents for peptide modification

Elija Grinhagena

Protein-protein interactions (PPIs) are responsible for regulating many biological processes in human bodies. PPIs often have a large binding site and often interact through an alpha helical segment. Therefore, the inhibition of PPIs can be difficult using ...

EPFL2023

Modular Synthesis of Benzocyclobutenes via Pd(II)-Catalyzed Oxidative [2+2] Annulation of Arylboronic Acids with Alkenes

Jieping Zhu, Anne-Clémence Corminboeuf, Qian Wang, Simone Gallarati, Takuji Fujii

Benzocyclobutenes (BCBs) are highly valuable compounds in organic synthesis, medicinal chemistry, and materials science. However, catalytic modular synthesis of functionalized BCBs from easily accessible starting materials remains limited. We report herein ...

2022

Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

Jérôme Waser, Stephanie Grace Elizabeth Amos

Ethynylbenziodoxolones (EBXs) have recently emerged as potent reagents for the alkynylation of radicals. Their combination with photocatalysis allows the synthesis of valuable alkynes at room temperature. Herein, we discuss two photomediated strategies for ...

2022

Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones

Jérôme Waser, Franck Le Vaillant, Stephanie Grace Elizabeth Amos

Alkynes and nitriles are valuable building blocks in organic synthesis and also have multiple applications in chemical biology and materials science. Due to the high availability of tertiary alcohols, developing methods for their conversion into alkynes an ...

2022

Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling to Ynimines: Development and Application to the Synthesis of Heterocycles

Jieping Zhu, Qiang Wang, Rémi Hugo Lavernhe

Nitrogen substituted alkynes such as ynamines and ynamides are versatile synthetic building blocks in organic chemistry. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high syntheti ...

Wiley-VCH Verlag GmbH2021

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

Development of remote C-H bond functionalization of redox-active alcohol derivatives and oxidative transformations under photoredox catalysis

Alexandre Julien Florent Leclair

The development of radical-based remote C(sp3)-H functionalizations of redox-active alcohol derivatives, oxidative cycloaddition and rearrangement transformations under visible light photocatalysis constitute the basis of this thesis. The first chapter des ...

EPFL2021

Covalent and Noncovalent Conjugation of Degradable Polymer Nanoparticles to T Lymphocytes

Harm-Anton Klok, Tanja Thomsen

Cells are attractive as carriers that can help to enhance control over the biodistribution of polymer nanomedicines. One strategy to use cells as carriers is based on the cell surface immobilization of the nanoparticle cargo. While a range of strategies ca ...

American Chemical Society2021

Asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces

Harald Brune, Samuel Thomas Stolz

Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. In this study, we address this issue by using structurally co ...

NATURE RESEARCH2021

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Surface functionalization of metal oxide harmonic nanoparticles for targeted cancer imaging

Raphaël Jovita De Matos

Cancer is a major health burden worldwide and the leading cause of death in industrialized countries. Early detection is a primary factor of survival and remission rate. Classical imaging methods such as magnetic resonance imaging, ultrasound imaging and m ...

EPFL2020

Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells

Jérôme Waser, Romain Gaëtan Tessier, Javier De Ceballos Cerrajeria, Raj Kumar Nandi

Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on ...

Wiley-VCH Verlag GmbH2020