Recent progress in alkynylation with hypervalent iodine reagents

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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

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

Ashis Kumar Das

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 ...

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

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

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Jérôme Waser, Franck Le Vaillant, Stephanie Grace Elizabeth Amos, Diana Cavalli

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alle ...

Wiley-VCH Verlag GmbH2021

Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

Jérôme Waser, Julien Aymeric Borrel

Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach e ...

2021

Copper‐Catalyzed Aza‐Sonogashira Cross‐Coupling to Ynimines: Development and Application to the Synthesis of Heterocycles

Jieping Zhu, Qiang Wang, Rémi Hugo Lavernhe

Nitrogen substituted alkynes such as ynamines and ynamides are versatile synthetic building blocks in organic chemistry. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high syntheti ...

Wiley-VCH Verlag GmbH2021

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

Bastian Antoine Rodolphe Claude Muriel

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 ...

EPFL2021

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

Diamine Synthesis via the Nitrogen-Directed Azidation of sigma- and pi-C-C Bonds

Jérôme Waser, Mingming Wang

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. ...

2021

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