Publications by Carl Thomas Bormann

Synthesis and Reactivity of a Terminal 1-Alkynyl Triazene

Kay Severin, Farzaneh Fadaei Tirani, Aude Trotti, Carl Thomas Bormann, Margarida Mayimona António, Christeena Mathew

2022

Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Kay Severin, Nicolai Cramer, Jin Fay Tan, Carl Thomas Bormann

The 1,1,2,2-tetrafluoroethylene unit is prevalent in bioactive molecules and functional materials. Despite being in principle a straightforward strategy to access this motif, the direct tetrafluorination of alkynes involves very hazardous or inconvenient r ...

2022

Synthesis of new 1-Vinyl and 1-Alkynyl Triazenes

Carl Thomas Bormann

The recent discovery of an N2O-based synthesis of triazenes in our group has enabled the synthesis and investigation of 1-alkynyl triazenes. Early studies showed their potential for a functional group tolerant synthesis of 1-vinyl triazenes, which is furth ...

EPFL2022

Synthesis of bicyclic vinyl triazenes by Ficini-type reactions

Kay Severin, Rosario Scopelliti, Farzaneh Fadaei Tirani, Carl Thomas Bormann

2021

Alkynyl triazenes enable divergent syntheses of 2-pyrones

Kay Severin, Nicolai Cramer, Jin Fay Tan, Carl Thomas Bormann

The 2-pyrone motif occurs frequently in bioactive natural products and is appreciated as synthetic intermediates. However, only few methods allow for diversifying functional group modifications on this relevant heterocycle. The distinct properties of 1-alk ...

2021

Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C–H Activation–Lossen Rearrangement–Wallach Reaction

Kay Severin, Nicolai Cramer, Jin Fay Tan, Carl Thomas Bormann

Fluorinated pyridones are an important scaffold displaying relevant biological activities. Efficient assembly strategies of pyridones are transition metal-catalyzed C–H annulations with alkynes. The inaccessibility and extreme lability of fluoro alkynes re ...

2020

Synthesis of Indenyl Triazenes by Rhodium-Catalyzed Annulation Reactions

Kay Severin, Rosario Scopelliti, Florian Gérald Abela, Farzaneh Fadaei Tirani, Carl Thomas Bormann

The synthesis of vinyl triazenes by metal-catalyzed processes is attractive, but only few examples have been described so far. Here, we describe Rh-catalyzed [3+2] annulation reactions of arylboronic acid derivatives and alkynyl triazenes. These reactions ...

2020

Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes

Kay Severin, Florian Gérald Abela, Nicolai Cramer, Frederick Mark Chadwick, Jin Fay Tan, Carl Thomas Bormann

Densely substituted fused aromatic triazenes can be prepared by [2 + 2 + 2] cyclotrimerization reactions of 1-alkynyl triazenes. The Cp*Ru-catalyzed cyclization proceeds well with both simple alkynyl triazenes and tethered 1-diynyl triazenes. Attractively, ...

2019