Concept

Alkyne

Related publications (199)

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

Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes

Jérôme Waser, Stefano Nicolai, Raha Sedigh-Zadeh

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins,constitute one of the most efficient methods to access them. In this ...

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

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

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, characterization and in vitro anticancer activity of highly cytotoxic trithiolato diruthenium complexes of the type [(eta(6)-p-(MeC6H4Pr)-Pr-i)(2)Ru-2(mu(2)-SR1)(2)(mu(2)-SR2)](+) containing different thiolato bridges

Paul Joseph Dyson, Catherine Marie Amélie Clavel

A series of cationic dinuclear p-cymene ruthenium complexes containing three thiolato bridges with different substituents at the sulfur atoms, (eta(6)-p-(MeC6H4Pr)-Pr-i)(2)Ru-2(mu(2)-SR1)(2)(mu(2)-SR2) (R-1 = CH2Ph, R-2 = Ph: 4; R-1 = CH2Ph, R-2 = p-( ...

Elsevier2013

Adducts of Nitrous Oxide and N-Heterocyclic Carbenes: Syntheses, Structures, and Reactivity

Rosario Scopelliti, Kay Severin, Euro Solari, Basile Vuichoud, Alexander Tskhovrebov

N-Heterocyclic carbenes (NHCs) react at ambient conditions with nitrous oxide to give covalent adducts. In the crystal, all compounds show a bent N2O group connected via the N-atom to the former carbene carbon atom. Most adducts are stable at room temperat ...

Amer Chemical Soc2013

Cascade Carbopalladation Reaction between Alkynes and gem-Dibromoolefins: Facile Access to Monoannelated Pentalenes

Pablo Rivera Fuentes

A carbopalladation cascade reaction of easily accessible gem-dibromoolefins and alkynes furnishes monobenzo- and mononaphthopentalenes. The new chromophores accessed by this short route exhibit small HOMO-LUMO gaps and redox amphoteric behavior with tunabl ...

2012

Development of Catalytic Umpolung

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

Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism

Rosario Scopelliti, Jérôme Waser, Jonathan Brand

This report describes a full study of the gold-catalyzed direct alkynylation of indoles, pyrroles, and thiophenes using alkynyl hypervalent iodine reagents, especially the study of the structural requirements of alkynyl benziodoxolones for an efficient ace ...

2012

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