Publication

Arylsilylation of Electron-Deficient Alkenes via Cooperative Photoredox and Nickel Catalysis

Related publications (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

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

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

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 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

Photochemical [2+2] Cycloaddition of Alkynyl Boronates

Jérôme Waser, Oleksandr Liashuk

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

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

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

Development of metal-organic frameworks based on N-heterocyclic ligands

Ilia Kochetygov

Metal-organic frameworks (MOFs) have firmly established in the field of porous materials since their early discovery in the 1990s. With a plethora of applications, these materials offer endless possibilities owing to their tunable, modular nature. The vast ...

EPFL2022

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

Anne-Clémence Corminboeuf, Qian Wang, Jieping Zhu, 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

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds

Ashis Kumar Das

Transition metal-catalyzed C-H activation is a powerful tool for the synthesis of organic building blocks, materials, and natural products. Over the last decade, directing-group-assisted metal-catalyzed C-H functionalization has attracted increasing intere ...

EPFL2022

Streamlined Alkylation via Nickel-Hydride-Catalyzed Hydrocarbonation of Alkenes

Xile Hu, Zhikun Zhang, Srikrishna Bera, Chao Fan

Compounds rich in sp(3)-hybridized carbons are desirable in drug discovery. Nickel-catalyzed hydrocarbonation of alkenes is a potentially efficient method to synthesize these compounds. By using abundant, readily available, and stable alkenes as pro-nucleo ...

2022

In depth analysis of heterogeneous catalysts for the chemoenzymatic dynamic kinetic resolution of beta-amino esters

Kumar Varoon Agrawal, Cédric Karel J Van Goethem

The chemoenzymatic dynamic kinetic resolution of beta-amino esters is established after detailed evaluation of metal-based heterogeneous catalysts for racemization and enzyme catalysts for kinetic resolution. Several heterogeneous palladium catalysts prove ...

ROYAL SOC CHEMISTRY2022

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

Atomic Level Insights of Non-Noble Metal Catalysts for the Oxygen Evolution Reaction

Lichen Bai

The conversion of intermittent renewable energy resources in the form of chemical bond, such as hydrogen production from electrochemical water splitting, is a promising way to satisfy the future global energy demand and address the environmental issues. Th ...

EPFL2021

Fluorene-based enamines as low-cost and dopant-free hole transporting materials for high performance and stable perovskite solar cells

Mohammad Khaja Nazeeruddin, Kasparas Rakstys, Albertus Adrian Sutanto, Maria Cristina Momblona Rincón

The power conversion efficiency of perovskite solar cells is approaching the Shockley-Queisser limit, and therefore this technology is next to the commercialization stage. Inexpensive and stable hole transporting materials are highly desirable for the succ ...

Royal Society of Chemistry2021

Stable Palladium Oxide Clusters Encapsulated in Silicalite-1 for Complete Methane Oxidation

Oliver Kröcher, Davide Ferri, Olga Safonova, Teng Li

Zeolite-supported metal catalysts are widely employed in a number of chemical processes, and the stability of the catalytically active species is one of the most critical factors determining the reaction performance. A good example is the Pd/zeolite cataly ...

AMER CHEMICAL SOC2021

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

The Genesis of Molecular Volcano Plots

Anne-Clémence Corminboeuf, Matthew Wodrich, Michael Markus Busch, Boodsarin Sawatlon

For the past two decades, linear free energy scaling relationships and volcano plots have seen frequent use as computational tools that aid in understanding and predicting the catalytic behavior of heterogeneous and electrocatalysts. Based on Sabatier's pr ...

2021

Silica-copper catalyst interfaces enable carbon-carbon coupling towards ethylene electrosynthesis

Michael Graetzel, Yelin Hu, Reza Zamani, Xiaoyan Wang, Dan Ren, Jun Li, Ziyun Wang, Yi Xu

Membrane electrode assembly (MEA) electrolyzers offer a means to scale up CO2-to-ethylene electroconversion using renewable electricity and close the anthropogenic carbon cycle. To date, excessive CO2 coverage at the catalyst surface with limited active si ...

Nature Research2021