Publications de Jérôme Waser

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Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compoun ...

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still chall ...

Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, ...

An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine(iii) diacetate (PIDA) in combination with BF3 center dot OEt2. The reaction gives access to a variety of valuable ...

With nitrogen too: The first catalytic [3+2] annulation of aminocyclopropanes with enol ethers is reported (see scheme; Phth=phthaloyl). The reaction worked with easily accessible phthalimidocyclopropanes using 5 mol % of SnCl4 in nearly quantitative yield ...

Cyclopropenes are the smallest unsaturated carbocycles. Removing one substituent from cyclopropenes leads to cyclopropenium cations (C3 + systems, CPCs). Stable aromatic pi-type CPCs were discovered by Breslow in 1957 by removing a substituent on the aliph ...

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladiumcatalyzed decarboxylative allylation of alpha-azido and cyano beta-ketoesters is reported. Indano ...

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 ...

An organic photoredox catalyst, 4CzIPN, was used in combination with a copper catalyst, CuCl, to effect decarboxylative C(sp3)–N coupling. The coupling worked with both anilines and imines as nitrogen sources and could be used to prepare a variety of alkyl ...

Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy finetuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this revi ...

In this Letter, we describe the synthesis of new donor-acceptor substituted cyclopropanes bearing various imido groups and their use in [3+2]-annulation reactions. A sequence of palladium-catalyzed vinylation and rhodium-catalyzed cyclopropanation gave acc ...

The chemical reactivity of 1-alkynyltriazenes has been investigated and is found to parallel the reactivity of ynamides. The similarity in reactivity of these two classes of compounds is demonstrated by addition reactions with acids, by cycloaddition react ...

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usin ...

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subcl ...

Gold-catalyzed domino processes constitute a useful alternative to C-H functionalization for the synthesis of functionalized (hetero)arenes. Herein, we report computational studies on the gold-catalyzed cyclization alkynylation of keto-allenes with ethynyl ...

We report an enantioselective palladium-catalyzed trans-hydroalkoxylation of propargylic amines with a trifluoroacetaldehydederived tether to build chiral oxazolidines. Diastereoselective hydrogenation using a heterogeneous palladium catalyst then gave acc ...

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 ...

The rapid and modular synthesis of the first bifunctional N-heterocyclic carbenes bearing a (thio)urea moiety as H-bond donor group was reported. Different analogues could be accessed in seven steps from cheap (S)-pyroglutamic acid in good overall yields ( ...

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 ...

Donor–acceptor cyclopropanes substituted with 3,3-dialkyltriazenyl groups are described herein. The strong electron-donating character of the triazene renders the cyclopropanes highly reactive, allowing for catalyst-free ring-opening reactions with methano ...

Jérôme Waser

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Intramolecular palladium-catalyzed alkene carboalkynylation

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole Transport Properties

A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of (±)-Trachelanthamidine

Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives

Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines

Accessing elusive σ-type cyclopropenium cation equivalents through redox gold catalysis

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

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

Tandem Photoredox and Copper-Catalyzed Decarboxylative C(sp3)–N Coupling of Anilines and Imines Using an Organic Photocatalyst

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions

1-Alkynyltriazenes as Functional Analogues of Ynamides

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

Gold-catalyzed domino cyclization-alkynylation reactions with EBX reagents: new insights into the reaction mechanism

Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C-H Bond Formation

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

Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Triazene-Activated Donor–Acceptor Cyclopropanes: Ring-Opening and (3 + 2) Annulation Reactions