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Concept

Diazo

Related publications (9)

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

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

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

Kay Severin, Farzaneh Fadaei Tirani, Iris Roswitha Landman

Nitrous oxide is a potential diazo transfer reagent, but its applications in organic chemistry are scarce. Here, we show that triazolopyridines and triazoloquinolines are formed in the reactions of metallated 2-alkylpyridines or 2-alkylquinolines with N2O. ...

Royal Society of Chemistry2021

Isolation and characterization of diazoolefins

Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Zhaowen Dong, Paul Varava

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 ...

2021

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

Guillaume Dominique Pisella

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 ...

EPFL2021

Copper-Catalyzed Oxyvinylation of Diazo Compounds

Jérôme Waser, Guillaume Dominique Pisella, Alec Gagnebin

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was su ...

2020

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

Jérôme Waser, Fides Benfatti, Florian Patrick Marie Daniel De la Barre De Nanteuil, Reto Frei, Filippo De Simone, Eloísa Sofía Serrano Robledo

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subcl ...

Royal Society of Chemistry2014

Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines

Jérôme Waser, Filippo De Simone

Activated cyclopropanes, such as vinyl and carbonyl cyclopropanes, are useful building blocks in organic chemistry due to their exceptional reactivity. This review focuses on the use of cyclopropyl carbonyls and imines in cyclization and cycloaddition reac ...

Georg Thieme Verlag2009

Catechol functionalized polymers and method for preparing them

Karl Gademann

Described are compounds that are capable of forming adlayers, said compounds comprising at least one headgroup A, an optional linker B, a polymer C, a terminal group D and an optionally present crosslinking group R, wherein the headgroup A is a compound of ...

2005