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Related publications (32)

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

Jérôme Waser, Matthew Wodrich, Franck Le Vaillant

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and no ...

2017

Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents

Jérôme Waser, Franck Le Vaillant

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild cond ...

2017

Introducing rigid pi-conjugated peripheral substituents in phthalocyanines for DSSCs

Michael Graetzel, Mohammad Khaja Nazeeruddin

A new carboxy-Zn(II) phthalocyanine bearing rigid 2,6-diarylphenyl peripheral substituents linked to the macrocycle through alkynyl spacers has been prepared by a convergent approach, which implies a triple Sonogashira coupling between the formyltriiodoZnP ...

World Sci Publ Co Inc2016

Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents

Jérôme Waser, Durga Prasada Rao Hari

Alkynes have found widespread applications in synthetic chemistry, biology, and materials sciences. In recent years, methods based on electrophilic alkynylation with hypervalent iodine reagents have made acetylene synthesis more flexible and efficient, but ...

American Chemical Society2016

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

Enantioselective Rhodium-catalyzed C-C Bond Activation of Cyclobutanones

Nicolai Cramer, Laetitia Marie Mélanie Souillart

The activation of carbon-carbon bonds has attracted much attention in the past decade. Despite important progress, the development of asymmetric reactions lags behind. For the first time, asymmetric rhodium(I)-catalyzed direct oxidative additions into enan ...

Swiss Chemical Soc2015

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

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

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

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

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

Jérôme Waser, Jonathan Brand, Davinia Fernández González

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

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

Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines

Jérôme Waser, Jonathan Brand

An efficient procedure was developed for the synthesis of 1-[(triisopropylsilyl)ethynyl]-1 lambda(3),2-benziodoxol-3(1H)-one on a 100-mmol (36-g) scale. The benziodoxolone can be used for the gold-catalyzed direct alkynylation of indole, 2-hexylthiophene, ...

2012

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