Publications related to Covalent Capture of Nitrous Oxide by N-Heterocyclic Carbenes

Isolation, Characterisation and Reactivity of N-Heterocyclic Diazoolefins

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 ...

EPFL2022

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

SET processes in Lewis acid–base reactions: the tritylation of N-heterocyclic carbenes

Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Andrzej Sienkiewicz, Cristian Pezzato, Zhaowen Dong

Reactions between N-heterocyclic carbenes (NHCs) and the trityl cation, [Ph3C]+, give covalent adducts of type [NHC–CPh3]+ and/or [NHC–C6H5–CPh2]+. EPR spectroscopy, UV-Vis analyses, and trapping experiments imply that adduct formation involves carbene rad ...

2020

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

Léonard Yannick Maurice Eymann

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 ...

EPFL2018

Developing Reactions of Strained Rings : Enantioselective Desymmetrization of meso-Diaminocyclopropanes and Annulation of Donor-Acceptor Aminocyclobutanes

Daniele Perrotta

Carbo- and heterocyclic structures containing nitrogen-substituted stereocenters are recurrent structural motifs in natural and bioactive compounds, therefore constituting a privileged class of synthetic targets. In this regard, substituted three- and four ...

EPFL2018

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Pierre Vogel

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 ...

2016

Synthesis of Azoimidazolium Dyes with Nitrous Oxide

Rosario Scopelliti, Kay Severin, Euro Solari, Alexander Tskhovrebov

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 ...

Wiley-Blackwell2015

Adducts of Nitrous Oxide and N-Heterocyclic Carbenes: Syntheses, Structures, and Reactivity

Rosario Scopelliti, Kay Severin, Euro Solari, Basile Vuichoud, Alexander Tskhovrebov

N-Heterocyclic carbenes (NHCs) react at ambient conditions with nitrous oxide to give covalent adducts. In the crystal, all compounds show a bent N2O group connected via the N-atom to the former carbene carbon atom. Most adducts are stable at room temperat ...

Amer Chemical Soc2013

Insertion of Zerovalent Nickel into the N–N Bond of N-Heterocyclic-Carbene-Activated N2O

Rosario Scopelliti, Kay Severin, Euro Solari, Alexander Tskhovrebov

Metal-mediated cleavage of the N–N bond is a rarely observed phenomenon in the chemistry of nitrous oxide (N2O). We demonstrate that, upon activation of N2O with N-heterocyclic carbenes, zerovalent nickel is able to insert into the N–N bond to give nitrosy ...

Amer Chemical Soc2013

Activation of Nitrous Oxide by Dinuclear Ruthenium Complexes

Rosario Scopelliti, Kay Severin, Euro Solari, Alexander Tskhovrebov

The dinuclear Ru(II) complexes (arene)Ru(μ-Cl)3RuCl(C2H4)(PCy3) (arene = p-cymene or 1,3,5-C6H3iPr3) react with N2O under mild conditions to give OPCy3 and the trinuclear complexes (arene)Ru(μ-Cl)3Ru(μ-Cl)3Ru(arene). The N-heterocyclic carbene complex (p-c ...

American Chemical Society2012