Publications associées à Sulfonamide and Tertiary Amine as Nucleophiles in Pd(II)-Catalyzed Diamination of Alkynes: Synthesis of Tetracyclic Indolobenzothiazine S,S‑Dioxides

Copper-catalyzed transformations of carboradicals generated by electrochemical and photochemical methods: oxidative amination and polyfluoroarylation

Organic radicals are highly active species that can undergo various transformations. Electrochemistry and photochemistry are efficient methods for the generation of these species of high energy, through single electron transfer processes under mild conditi ...

EPFL2021

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

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Xile Hu, Runze Mao, Xiangli Yi, Lara Lavrencic

Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carbox ...

Wiley-VCH Verlag GmbH2021

Development of New Strategies of Umpolung with Cyclic Hypervalent Iodine Reagents

Paola Caramenti

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from s ...

EPFL2019

Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis

Xile Hu, Jonathan Balon, Runze Mao

Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal‐catalyzed cross‐coupling of alkyl electrophiles with nitrogen nucleophiles. ...

Wiley-VCH Verlag GmbH2018

Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence

Qian Wang, Jieping Zhu, Shuo Tong

Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom syntho ...

Wiley-Blackwell2016

Synthesis of Alkynylated Heterocycles by Direct C-H Alkynylation or Domino Alkynylation Reactions

Yifan Li

Heterocycles are important compounds in organic chemistry. To introduce functional groups on heterocycles or synthesize functionalized heterocycles stays a hot topic of research. Among all the functional groups, alkynes attracted a lot of attention not onl ...

EPFL2016

Synthesis and structure-activity studies of well-defined nickel complexes as catalysts for cross coupling of alkyl electrophiles

Pablo Marcelo Perez Garcia

This dissertation is devoted to the development of well-defined nickel complexes as catalysts for cross coupling processes of alkyl electrophiles. In chapter one, we summarize recent cross coupling methodologies of alkyl electrophiles using nickel based ca ...

EPFL2015

"New methods for indoles and [3,4]-fused oxindoles syntheses" and "Copper-catalyzed/mediated difunctionalization of alkenes with alkylnitriles"

Ala Bunescu

Two main topics were addressed in this manuscript: (1) New methods for indoles and [3,4]-fused oxindoles syntheses; (2) Copper-catalyzed/mediated difunctionalization of alkenes with alkylnitriles. Given the omnipresent character of the indole and oxindole ...

EPFL2014

Development of Catalytic Umpolung : Part 1: Direct Alkynylation of Heterocycles and Electron-Rich Aromatics using Alkynyl-Benziodoxolones - Part 2: Synthesis of New Bifunctional (Thio)urea-Carbene Catalysts

Jonathan Brand

The development of efficient synthetic methodologies is crucial to access complex molecules in an economic, eco-friendly and safe way. The reversal of the intrinsic reactivity of functional groups, called Umpolung, allows alternative synthetic strategies a ...

EPFL2012

Chemoselective C-H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C-C Cross-Coupling of Tertiary Amines with Terminal Alkynes. Reaction Scope and Mechanism

Pierre Vogel, Chandra Mouleeswara Rao Volla

FeCl2 catalyzes the oxidative C-C cross-coupling of tertiary amines with terminal alkynes into propargylamines using (t-BuO)2 as oxidant. The reaction can be applied to aromatic and aliphatic amines and alkynes without solvent. High chemoselectivity for am ...

2009

Autoxidation of a 4-iminoimidazolidin-2-one with a tertiary 5-hydrogen to its 5-hydroxy derivative

Anne-Sophie Chauvin

Chemoselective autoxidation of 4-imino-1,5-dimethyl-3-(4-nitrophenyl) imidazolidin-2-one (1b) to its 5-hydroxy derivative 2 occurred in solutions of DMSO-d(6), acetonitrile-d(3) or refluxing ethanol. Also bis(imidazolidin-5-yl) peroxide 5 was isolated as a ...

2008