Publications related to Alkene

Well-Defined Ti Surface Sites in Ziegler-Natta Pre-Catalysts from 47/49Ti Solid-State Nuclear Magnetic Resonance Spectroscopy

Treatment of Ziegler-Natta (ZN) catalysts with BCl3 improves their activity by increasing the number of active sites. Here we show how Ti-47/49 solid-state nuclear magnetic resonance (NMR) spectroscopy enables us to understand the electronic structure of t ...

Amer Chemical Soc2024

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

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

Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles

Jérôme Waser, Matthew Wodrich, André Bossonnet

We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...

2023

Cycloalkane Oxidation Catalyzed by Copper-based Catalysts with H2O2 under Mild Conditions

Nukorn Plainpan, Jantira Chimlert

Copper-catalyzed cycloalkane oxidation using H2O2 as an oxidant was investigated under mild conditions. The copper catalysts studied in this work ranged from commercially-available copper(II) salts to copper(II) complexes containing polypyridyl ligands. Va ...

WILEY-V C H VERLAG GMBH2023

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

Diverting the 5-exo-Trig Oxypalladation to Formally 6-endo-Trig Fluorocycloetherification Product through 1,2-O/Pd(IV) Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Jing Gong

Pd-catalyzed cyclizative functionalization of γ-hydroxyalkenes affords tetrahydrofuran derivatives via a key 5-exo-trig oxypalladation step. Herein, we report a palladium(II)-catalyzed, Selectfluor-mediated formal 6-endo-trig fluorocycloetherification of γ ...

2023

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

Complexation Strategies towards Challenging Group 9 Metal Cyclopentadienyl Scaffolds

Aragorn Nathan Laverny

Cyclopentadienyl (Cp) metal complexes and their chiral counterparts (CpX) have enabled the development of challenging C-H activation transformations. While major progresses were made in developing new chiral CpX complexes and exploring their reactivity, th ...

EPFL2023

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

Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe

Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...

Wiley-VCH Verlag GmbH2023

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

The fundamental relation between electrohelicity and molecular optical activity

Anne-Clémence Corminboeuf, Marc Hamilton Folkmann Garner

Electrohelicity arises in molecules such as allene and spiropentadiene when their symmetry is reduced and helical frontier molecular orbitals (MOs) appear. Such molecules are optically active and electrohelicity has been suggested as a possible design prin ...

ROYAL SOC CHEMISTRY2023

Streamlined Alkylation via Nickel-Hydride-Catalyzed Hydrocarbonation of Alkenes

Xile Hu, Chao Fan, Srikrishna Bera, Zhikun Zhang

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

Green solvents for chemical reactions

Jeremy Luterbacher, Anastasiia Komarova

The present invention relates to Use of a compound of the general formula (I), (II), (III), (IV), (V) or (VI) wherein R1 and R1', R21 and R21', R31 and R31' are the same and are hydrogen, a linear or branched C1 to C18 alkyl, a linear or branched C2 to C18 ...

2022

Enantio- and diastereoselective construction of vicinal C(sp(3)) centres via nickel-catalysed hydroalkylation of alkenes

Xile Hu, Chao Fan, Srikrishna Bera

In drug discovery, the proportion of aliphatic carbons (C(sp(3))) and the presence of chiral carbons in organic molecules are positively correlated to their chance of clinical success. Although methods exist for the synthesis of chiral C(sp(3))-rich molecu ...

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

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

Jérôme Waser, Stefano Nicolai, Ashis Kumar Das, Thomas Rossolini

A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturate ...

2022

Revisiting the Impact of Morphology and Oxidation State of Cu on CO2 Reduction Using Electrochemical Flow Cell

Michael Graetzel, Shaik Mohammed Zakeeruddin, Jing Gao, Dan Ren

Electroreduction of carbon dioxide (CO2) in a flow electrolyzer represents a promising carbon-neutral technology with efficient production of valuable chemicals. In this work, the catalytic performance of polycrystalline copper (Cu), Cu2O-derived copper (O ...

AMER CHEMICAL SOC2022

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

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

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

Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary

Jérôme Waser, Mikus Purins

For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...

Wiley-VCH Verlag GmbH2022