Publications related to Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds

Related publications (34)

Photomediated aliphatic C-H functionalization

The C–H functionalization of inert alkanes has long been one of the most challenging reactions in organic synthesis. Now, the use of hypervalent iodine reagents has enabled the diverse functionalization of various aliphatic C–H bonds under blue light irrad ...

NATURE PORTFOLIO2025

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

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

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, Vu Trung Tin Nguyen

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

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

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

A Simple, Transition Metal Catalyst-Free Method for the Design of Complex Organic Building Blocks Used to Construct Porous Metal-Organic Frameworks

Wendy Lee Queen, Ilia Kochetygov, Till Marian Schertenleib, Jordi Espin Marti, Anita Justin, Jocelyn Richard Roth, Nazanin Taheri

The design of metal-organic frameworks (MOFs) having large pore sizes and volumes often requires the use of complex organic ligands, currently synthesized using costly and time-consuming palladium-catalyzed coupling chemistry. Thus, in the present work, a ...

Wiley-VCH Verlag GmbH2023

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

Ni-Based Nanoparticles Catalyzed Hydrodeoxygenation of Ketones, Ethers, and Phenols to (Cyclo) Aliphatic Compounds

Paul Joseph Dyson, Yelin Hu, Mingyang Liu

Catalytic hydrodeoxygenation is of prime importance in the valorization of biomass-based feedstocks to produce essential chemicals and fuels. To carry out this process in a more cost-effective and sustainable manner, the use of 3D-metal-based nanostructure ...

Amer Chemical Soc2023

Ozonation of organic compounds in water and wastewater: A critical review

Urs von Gunten, Sung Eun Lim

Ozonation has been applied in water treatment for more than a century, first for disinfection, later for oxidation of inorganic and organic pollutants. In recent years, ozone has been increasingly applied for enhanced municipal wastewater treatment for eco ...

PERGAMON-ELSEVIER SCIENCE LTD2022

Synthetic chemistry with nitrous oxide and triazenes

Iris Roswitha Landman

Nitrous oxide (N2O) has gained much interest because of its physiological effects ("laughing gas") and its negative environmental impact ("greenhouse gas", "ozone-depleting substance"): It has a lifetime of more than 100 years in the atmosphere. Its persis ...

EPFL2022

Simultaneous Generation of Methyl Esters and CO in Lignin Transformation

Paul Joseph Dyson, Mingyang Liu

Lignin is an abundant renewable carbon source. Due to its complex structure, utilization of lignin is very challenging. Herein, we describe an efficient strategy for the simultaneous utilization of lignin, in which the methoxy groups in lignin react with c ...

Wiley-VCH Verlag GmbH2022

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

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

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

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Qian Wang, Jieping Zhu, Alexandre Julien Florent Leclair

A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these pi-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenone ...

AMER CHEMICAL SOC2022

Apparent 6-endo-trig Carbofluorination of Alkenes Enabled by Palladium-Based Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Jing Gong

Alkene difunctionalization featuring an intramolecular carbometallation step has been developed into a powerful transformation in organic synthesis. The 5-exo-trig carbometallation is in general highly favored over the alternative 6-endo-trig cyclization. ...

Wiley-VCH Verlag GmbH2022

Characterization of primary and aged wood burning and coal combustion organic aerosols in an environmental chamber and its implications for atmospheric aerosols

Satoshi Takahama, Nikunj Dudani, Amir Yazdani

Particulate matter (PM) affects visibility, climate, and public health. Organic matter (OM), a uniquely complex portion of PM, can make up more than half of total atmospheric fine PM mass. We investigated the effect of aging on secondary organic aerosol (S ...

European Geosciences Union2021