Publications related to Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

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

Excited State-Specific CASSCF Theory for the Torsion of Ethylene

State-specific complete active space self-consistent field (SS-CASSCF) theory has emerged as a promising route to accurately predict electronically excited energy surfaces away from molecular equilibria. However, its accuracy and practicality for chemical ...

Amer Chemical Soc2024

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

Qian Wang, Jieping Zhu, Qiang Feng, Chenxu Liu

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

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

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

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

Synthesis, isolation and application of a sila-ketenyl anion

Rosario Scopelliti, Shiori Fujimori

Ynolates or ketenyl anions, [RCCO]-, are negatively charged reactive intermediates, which can be generated in situ and used for divergent chemical transformations. Ynolates can react either at the oxygen or carbon centres or across the C-C triple bond, mak ...

Springernature2023

Double-bond delocalization in non-alternant hydrocarbons induces inverted singlet-triplet gaps

Anne-Clémence Corminboeuf, Jacob Terence Blaskovits, Marc Hamilton Folkmann Garner

Molecules where the first excited singlet state is lower in energy than the first excited triplet state have the potential to revolutionize OLEDs. This inverted singlet-triplet gap violates Hund's rule and currently there are only a few molecules which are ...

ROYAL SOC CHEMISTRY2023

Double-bond delocalization in non-alternant hydrocarbons induces inverted singlet-triplet gaps

Anne-Clémence Corminboeuf, Jacob Terence Blaskovits, Marc Hamilton Folkmann Garner

Molecules where the first excited singlet state is lower in energy than the first excited triplet state have the potential to revolutionize OLEDs. This inverted singlet-triplet gap violates Hund's rule and currently there are only a few molecules which are ...

ROYAL SOC CHEMISTRY2023

Tunnel junction sensing of TATP explosive at the single-molecule level

Radomir Zikic, Helena Miljkovic

Triacetone triperoxide (TATP) is a highly potent homemade explosive commonly used in terrorist attacks. Its detection poses a significant challenge due to its volatility, and the lack of portability of current sensing techniques. To address this issue, we ...

Royal Soc Chemistry2023

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

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

Unveiling facet-dependent degradation and facet engineering for stable perovskite solar cells

Michael Graetzel, Felix Thomas Eickemeyer

A myriad of studies and strategies have already been devoted to improving the stability of perovskite films; however, the role of the different perovskite crystal facets in stability is still unknown. Here, we reveal the underlying mechanisms of facet-depe ...

American Association for the Advancement of Science2023

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Jérôme Waser, Eliott Hugo Joran Le Du, Julien Aymeric Borrel

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most f ...

2022

Helical versus linear Jahn-Teller distortions in allene and spiropentadiene radical cations

Anne-Clémence Corminboeuf, Marc Hamilton Folkmann Garner, Rubén Laplaza Solanas

The allene radical cation can be stabilized both by Jahn-Teller distortion of the bond lengths and by torsion of the end-groups. However, only the latter happens and the allene radical cation relaxes into a twisted D-2 symmetry structure with equal double- ...

ROYAL SOC CHEMISTRY2022

Photochemical Alkynylations with Hypervalent Iodine Reagents

Stephanie Grace Elizabeth Amos

Over the past twenty years, photochemical transformations have gained in importance in organic chemistry. Indeed, the development of photocatalysts has allowed the use of visible light as an energy source for chemical transformations. More specifically, ph ...

EPFL2022

Mechanistic Insight into Supramolecular Polymerization in Water Tunable by Molecular Geometry

Lukas Pfeifer

Supramolecular self-assembly in water based on non-covalent bonding is attracting major attention due to the potential of hydrogels and aqueous polymers in biomedical applications. Although supramolecular polymerization in organic solvents is well establis ...

CHINESE CHEMICAL SOC2022

N-Terminal Selective C-H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

Jérôme Waser, Raphaël Michel Henri Simonet-Davin, Emmanuelle Madeline Dominique Allouche

A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at th ...

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

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Mingming Wang

Nitrogen-containing compounds are an important class of molecules in medicinal chemistry, chemical biology, biochemistry, material sciences or environmental sciences. Organic nitrogen occurs in many forms, ranging from small building blocks such as urea, a ...

EPFL2022

Copper-catalyzed transformations of carboradicals generated by electrochemical and photochemical methods: oxidative amination and polyfluoroarylation

Xiangli Yi

Organic radicals are highly active species that can undergo various transformations. Electrochemistry and photochemistry are efficient methods for the generation of these species of high energy, through single electron transfer processes under mild conditi ...

EPFL2021

Alkynyl triazenes enable divergent syntheses of 2-pyrones

Kay Severin, Nicolai Cramer, Jin Fay Tan, Carl Thomas Bormann

The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alk ...

2021