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

Related publications (35)

Exploring the reactivity of N-heterocyclic diazoolefins

Diazo compounds of the type R1R2CN2 are widely used in organometallic catalysis and synthetic chemistry. Stable diazoolefins, R1R2C=CN2, have only been isolated recently. Diazoolefins undergo cycloaddition reactions and tend to be carbon donors when used a ...

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

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Jérôme Waser, Matthew Wodrich, Xiangdong Li

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

2024

Palladium-based supramolecular assemblies: from complex structures to water-soluble anion-receptors

Sylvain Alexandre Marie Sudan

The combination of palladium salts and bipyridyl ligands can lead to the formation of a large variety of coordination complexes, with different shapes and sizes, displaying a very versatile host-guest chemistry. Increasing their structural complexity remai ...

EPFL2024

Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes

Jérôme Waser, Stefano Nicolai

Bicyclic carbocycles containing a high fraction of Csp3 have become highly attractive synthetic targets because of the multiple applications they have found in medicinal chemistry. The formal cycloaddition of bicyclobutanes (BCBs) with two- or three-atom p ...

Royal Soc Chemistry2024

Arylative Ring Expansion of 3-Vinylazetidin-3-Ols and 3-Vinyloxetan-3-Ols to Dihydrofurans by Dual Palladium and Acid Catalysis

Qian Wang, Jieping Zhu, Takuji Fujii

In contrast to the well-studied 1-vinylcyclobu- tanols, the reactivity of 3-vinylazetidin-3-ols 1 and 3- vinyloxetan-3-ols 2 under transition metal catalysis remains largely unexplored. We report herein their unique reactivity under dual palladium and acid ...

Wiley-VCH Verlag GmbH2024

Editing Tetrasubstituted Carbon: Dual C–O Bond Functionalization of Tertiary Alcohols Enabled by Palladium-Based Dyotropic Rearrangement

Tristan Corentin Pierre Delcaillau, Jieping Zhu, Qian Wang, Baochao Yang

Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent ...

2024

Regiodivergent and Enantioselective Synthesis of Cyclic Sulfones via Ligand-Controlled Nickel-Catalyzed Hydroalkylation

Jennifer Morel, Xile Hu, Chao Fan, Uttam Dhawa, Deyun Qian

Cyclic sulfones have demonstrated important applications in drug discovery. However, the catalytic and enantioselective synthesis of chiral cyclic sulfones remains challenging. Herein, we develop nickel-catalyzed regiodivergent and enantioselective hydroal ...

Wiley-VCH Verlag GmbH2024

The effect of Ni- and Mo-based materials on thermochemical sulfate reduction by glycerol under hydrothermal process conditions

Oliver Kröcher, Cheng Chang

Catalytic hydrothermal gasification (cHTG) is a sustainable and promising route to convert wet biomass into renewable methane, but the catalyst is deactivated by small amounts of soluble sulfate stemming from the biomass feedstock. Under hydrothermal condi ...

Elsevier2024

Functionalization of harmonic nanoparticles for drug release and multimodal imaging applications

Adrian Stefan Gheata

Cancer is among the leading causes of death worldwide, and as knowledge of the disease continues to grow there is an increasing interest towards precision medicine: more specifically towards the theranostics field, i.e the development of targeted molecular ...

EPFL2024

Deoxygenative Transformation of Alcohols via Phosphoranyl Radical from Exogenous Radical Addition

Xile Hu, Tao Xu, Chao Fan

A general approach to the direct deoxygenative transformation of primary, secondary, and tertiary alcohols has been developed. It undergoes through phosphoranyl radical intermediates generated by the addition of exogenous iodine radical to trivalent alkoxy ...

Wiley-VCH Verlag GmbH2024

Biobased surfactant

Jeremy Luterbacher, Stefania Bertella, Songlan Sun, Anastasiia Komarova

The present invention relates to a compound of the general formula (I), (II) and (III), more specifically of formula (Ia), (Ib), (Ic)wherein R11 and R12 or R21 and R22 or R31 and R32 are both hydrogen or form together with CHR50 a cyclic moiety or one of R ...

2024

The Mn(VII)-H2O2 oxidation process: Abatement of electron-deficient N-containing organic compounds

Urs von Gunten

Chemical oxidants applied in water treatment are electrophiles, which preferentially attack sites with higher electron density. This typically results in less efficient oxidative abatement of organic compounds with electronwithdrawing substituents. In this ...

Elsevier Science Sa2024

Controlling On-Surface Photoactivity: The Impact of π-Conjugation in Anhydride-Functionalized Molecules on a Semiconductor Surface

Christian Wäckerlin

On-surface synthesis has become a prominent method for growing low-dimensional carbon-based nanomaterials on metal surfaces. However, the necessity of decoupling organic nanostructures from metal substrates to exploit their properties requires either trans ...

Wiley-VCH Verlag GmbH2024

Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction

Chenxu Liu, Qiang Feng, Jieping Zhu, Qian Wang

We report in this paper a Pd(II)-catalyzed migratory gem-fluorolactonization of ene-carboxylic acids. Reaction of 4-methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in go ...

Wiley-VCH Verlag GmbH2024

Reactions of hypobromous acid with dimethyl selenide, dimethyl diselenide and other organic selenium compounds: kinetics and product formation

Urs von Gunten

Selenium (Se) is an essential micronutrient for many living organisms particularly due to its unique redox properties. We recently found that the sulfur (S) analog for dimethyl selenide (DMSe), i.e. dimethyl sulfide (DMS), reacts fast with the marine oxida ...

Royal Soc Chemistry2024

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

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

Tuning the reactivity of uranium towards small molecules in multimetallic complexes

Nadir Jori

One of the main goals of organometallic chemistry in the last decades was the activation of small molecule in mild reaction conditions. Even though multiple examples of catalytic cycles able to produce fine chemicals from cheap and abundant sources using t ...

EPFL2023

Recent progress in alkynylation with hypervalent iodine reagents

Jérôme Waser, Eliott Hugo Joran Le Du

Although alkynes are one of the smallest functional groups, they are among the most versatile building blocks for organic chemistry, with applications ranging from biochemistry to material sciences. Alkynylation reactions have traditionally relied on the u ...

Royal Society of Chemistry2023