Nitrous oxide as a diazo transfer reagent: the synthesis of triazolopyridines

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Frustrated Lewis pairs (FLPs), featuring reactive combinations of Lewis acids and Lewis bases, have been utilized for myriad metal-free homogeneous catalytic processes. Immobilizing the active Lewis sites to a solid support, especially to porous scaffolds, ...

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 ...

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 ...

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 ...

Examples for applications of nitrous oxide in organic synthesis remain rare up until today. First mayor contributions of our group were published in 2012, when nitrous oxide was successfully captured by N-heterocyclic carbenes. Subsequent studies investiga ...

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 ...

Diazoolefins tend to be highly reactive compounds that rapidly lose dinitrogen. So far, most experimental evidence for diazoolefins is indirect, via trapping experiments. Here we show that diazoolefins are observed to form in reactions of N-heterocyclic ol ...

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 ...

The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new s ...

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 ...

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

N-Heterocyclic carbenes are able to form covalent adducts with nitrous oxide (N2O) under ambient conditions. This thesis summarizes the studies of these adducts and their reactivity. A ditopic carbanionic N-heterocyclic carbene was found to react with nit ...

The chemistry of aromatic triazenes is well known, and has been explored for more than a century. These compounds have emerged as very useful intermediates, because of their unique reactivity. This functionality can notably be used to access many other fun ...

N-formylation of amines with CO2 and hydrosilane reducing agents proceeds via fast and complex chemical equilibria, which hinder easy analysis of the reaction pathways. In situ reaction monitoring and kinetic studies reveal that three proposed pathways, vi ...

Organic molecules are indispensable have greatly contributed to the confort of our modern life. Nevertheless, humanity is facing now new challenges such as environmental issues and emerging drug resistances. In order to solve these major concerns, chemists ...

Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organi ...

Transition-metal-catalyzed hydrosilylation of olefins is one of the most important methods for the preparation of organosilicon compounds, which have broad applications in both synthetic and material chemistry. For decades, precious metals, principally pla ...

Triazenes are valuable compounds in organic chemistry and numerous applications have been reported. Furthermore, triazenes have been investigated extensively as potential antitumor drugs. Here, we describe a new method for the synthesis of triazenes. The p ...

A new method for the synthesis of industrially important azoimidazolium dyes is presented. The procedure is based on a reagent which is rarely used in the context of synthetic organic chemistry: nitrous oxide (“laughing gas”). N2O is first coupled to N-het ...

Nitrous oxide as a diazo transfer reagent: the synthesis of triazolopyridines

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Engineering Frustrated Lewis Pair Active Sites in Porous Organic Scaffolds for Catalytic CO2 Hydrogenation

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Synthetic chemistry with nitrous oxide and triazenes

Ring-Opening Reactions of Aminocyclopropanes and Aminocyclobutanes

Isolation, Characterisation and Reactivity of N-Heterocyclic Diazoolefins

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

Isolation and characterization of diazoolefins

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2

Dyes, Radicals and Nitrous Oxide Adducts Derived from N-Heterocyclic Carbenes

Investigations of the Chemistry of 1-Alkynyltriazenes

Mechanistic Study of the N-Formylation of Amines with Carbon Dioxide and Hydrosilanes

Lewis acid Catalyzed Annulations of Donor-Acceptor Aminocyclopropanes and Aminocyclobutanes

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Nickel-catalyzed Hydrosilylation of Alkenes and Transition-Metal-Free Intermolecular α-C-H Amination of Ethers

Synthesis of Triazenes with Nitrous Oxide

Synthesis of Azoimidazolium Dyes with Nitrous Oxide