Publications related to Pd-Catalyzed Intramolecular Oxyalkynylation of Alkenes with Hypervalent Iodine

Related publications (30)

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

Macrocycles have raised much interest in the pharmaceutical industry due to their ability to bind challenging targets while often still being able to cross membranes to reach intracellular proteins. However, the development of macrocyclic ligands to new di ...

EPFL2023

Hypervalent Iodine: New Reagents and Functionalization of Peptides

Eliott Hugo Joran Le Du

Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ide ...

EPFL2023

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

Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

Jérôme Waser, Stephanie Grace Elizabeth Amos

Ethynylbenziodoxolones (EBXs) have recently emerged as potent reagents for the alkynylation of radicals. Their combination with photocatalysis allows the synthesis of valuable alkynes at room temperature. Herein, we discuss two photomediated strategies for ...

2022

Stable Palladium Oxide Clusters Encapsulated in Silicalite-1 for Complete Methane Oxidation

Oliver Kröcher, Davide Ferri, Olga Safonova

Zeolite-supported metal catalysts are widely employed in a number of chemical processes, and the stability of the catalytically active species is one of the most critical factors determining the reaction performance. A good example is the Pd/zeolite cataly ...

AMER CHEMICAL SOC2021

Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water

Jérôme Waser, Durga Prasada Rao Hari, Romain Gaëtan Tessier, Abhaya Kumar Mishra

We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent o ...

Wiley-VCH Verlag GmbH2021

Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals

Guido Barzanò

C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...

EPFL2020

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Alexy Robert Bonnin, Paul Joseph Dyson, Simon Nussbaum, Martin Hulla

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the c ...

Royal Society of Chemistry2019

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers

Jérôme Waser, Matthew Wodrich, Paola Caramenti, Nina Declas, Romain Gaëtan Tessier

Enamides and enol ethers are valuable building blocks in synthetic chemistry, yet their stereoselective synthesis can be challenging. Herein, we report a new stereoselective synthesis of vinyl, aryl, alkynyl, alkyl and thio-substituted Z-enamides and enol ...

2019

Organocatalysts in C-N Bond Forming Reactions of Amines with CO2

Martin Hulla

The thesis describes a simple approach for N-formylation of amines with CO2 and hydrosilane reducing agents, the use of organic salts as N-formylation catalysts, their physical properties required for high catalytic activity and their role in the catalytic ...

EPFL2019

Influence of the Anion on the Oxidation of 5-Hydroxy-methylfurfural by Using Ionic-Polymer-Supported Platinum Nanoparticle Catalysts

Paul Joseph Dyson, Zhaofu Fei, Ning Yan, Felix Daniel Bobbink, Sviatlana Siankevich

Platinum nanoparticles stabilized by an imidazolium-based cross-linked polymer (with chloride as the counteranion) efficiently catalyzed the oxidation of 5-hydroxymethylfurfural to form 2,5-furandicarboxylic acid in water under mild conditions with oxygen ...

2018

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

Jérôme Waser, Stefano Nicolai, Paola Caramenti

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 degrees C and were applied in the C-H arylation of unactivated arene ...

2017

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions

Jieping Zhu, Qian Wang, Wangqing Kong

Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3)-Pd intermediate using diboron–water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectiviti ...

Wiley-Blackwell2017

Skyrmion formation in a bulk chiral magnet at zero magnetic field and above room temperature

Henrik Moodysson Rønnow, Jonathan White

We report that in a β-Mn-type chiral magnet Co9Zn9Mn2, skyrmions are realized as a metastable state over a wide temperature range, including room temperature, via field cooling through the thermodynamic equilibrium skyrmion phase that exists below a transi ...

2017

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

Catalytic Applications and Mechanistic Investigations of Iron Bis(oxazolinylphenyl)amino Pincer Complexes in Kumada Cross Coupling and Hydrosilylation Reactions

Gerald Bauer

The aim of the project was to investigate iron bis(oxazolinylphenyl)amino (bopa) pincer complexes as pre-catalysts in the enantioselective Kumada cross-coupling of non-activated alkyl halides with aryl Grignard reagents. From this preliminary cross-couplin ...

EPFL2015

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

Jérôme Waser, Franck Le Vaillant, Thibaut Christian Courant

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

Cross-Coupling of Nonactivated Primary and Secondary Alkyl Halides with Aryl Grignard Reagents Catalyzed by Chiral Iron Pincer Complexes

Xile Hu, Chi Wai Cheung, Gerald Bauer

Iron(III) bisoxazolinylphenylamido (bopa) pincer complexes are efficient precatalysts for the cross-coupling of nonactivated primary and secondary alkyl halides with phenyl Grignard reagents. The reactions proceed at room temperature in moderate to excelle ...

Georg Thieme Verlag2015

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

Mechanistic Studies Related to Nickel-Catalyzed Alkyl-Alkyl Cross Coupling Reactions

Jan Breitenfeld

Cross-coupling reactions of non-activated alkyl halides are potentially useful chemical transformations. At the same time, however, they are challenging due to a series of unproductive side reactions. Recently, significant progress has been made to overcom ...

EPFL2013