Publication

Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines

Publications associées (32)

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017

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

Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents

Jérôme Waser, Thibaut Christian Courant, Franck Le Vaillant

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes fro ...

Wiley-Blackwell2015

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

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents

Jérôme Waser, Chia-Chun Chen

Highly efficient protocols for the alkynylation of H-phosphi(na)tes and secondary phosphine oxides with silyl, aryl and alkyl ethynyl-benziodoxolone (EBX) reagents are reported. Alkynyl phosphorus compounds were obtained in 69-93% yield without the need fo ...

Royal Society of Chemistry2014

Mild and Phosphine-Free Iron-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides with Alkynyl Grignard Reagents

Xile Hu, Peng Ren, Chi Wai Cheung

A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to af ...

American Chemical Society2014

Zinc-gold cooperative catalysis for the direct alkynylation of benzofurans

Jérôme Waser, Yifan Li

The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. H ...

2013

C2-Selective Direct Alkynylation of Indoles

Stephanie Ganss, Jérôme Waser, Jonathan Brand, Gergely Laszlo Tolnai

The first C2-selective alkynylation of indoles using the hypervalent iodine reagent triisopropylsilylethyny1-1,2-benziodoxol-3(1H)-one (TIPS-EBX) with Pd(II) as a catalyst is described. This convenient and robust method gives a single-step access to substi ...

American Chemical Society2013

Gold-Catalyzed Alkynylation: Acetylene-Transfer instead of Functionalization

Jérôme Waser, Jonathan Brand, Yifan Li

Over the last fifteen years, gold has been raised from the status of an inert noble metal to one of the most-often-used catalysts in synthetic chemistry. The functionalization of the triple bond of alkynes has been especially successful in this respect. In ...

Wiley-V C H Verlag Gmbh2013

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates

Davinia Fernández González, Jérôme Waser, Jonathan Brand

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scanning ...

Wiley-Blackwell2013

A Highly Chemoselective and Practical Alkynylation of Thiols

Jérôme Waser, Reto Frei

A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagen ...

American Chemical Society2013

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