Publications related to Alkyne

Synthesis, isolation and application of a sila-ketenyl anion

Ynolates or ketenyl anions, [RCCO]-, are negatively charged reactive intermediates, which can be generated in situ and used for divergent chemical transformations. Ynolates can react either at the oxygen or carbon centres or across the C-C triple bond, mak ...

London2023

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 ...

SWISS CHEMICAL SOC2022

Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones

Jérôme Waser, Franck Le Vaillant, Stephanie Grace Elizabeth Amos

Alkynes and nitriles are valuable building blocks in organic synthesis and also have multiple applications in chemical biology and materials science. Due to the high availability of tertiary alcohols, developing methods for their conversion into alkynes an ...

WILEY-V C H VERLAG GMBH2022

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Jérôme Waser, Eliott Hugo Joran Le Du, Julien Aymeric Borrel

We report a copper-catalyzed alkynylation of azadipeptides using ethynylbenziodoxolone (EBX) reagents. Nonsymmetrical ynehydrazides could be obtained in 25–97% yield using azaglycine derivatives as nucleophiles. The transformation is compatible with most f ...

2022

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Qian Wang, Jieping Zhu, Alexandre Julien Florent Leclair

A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these pi-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenone ...

AMER CHEMICAL SOC2022

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

Jérôme Waser, Stefano Nicolai, Ashis Kumar Das, Thomas Rossolini

A Pd-catalyzed method based on the use of a molecular tether is described for olefin difunctionalization. Enabled by an easily introduced trifluoroacetaldehyde-derived tether, a simultaneous introduction of oxygen and nitrogen heteroatoms across unsaturate ...

2022

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

Jérôme Waser, Mikus Purins, Ashis Kumar Das, Luca Buzzetti

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 ...

AMER CHEMICAL SOC2022

Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Kay Severin, Nicolai Cramer, Carl Thomas Bormann, Jin Fay Tan

The 1,1,2,2-tetrafluoroethylene unit is prevalent in bioactive molecules and functional materials. Despite being in principle a straightforward strategy to access this motif, the direct tetrafluorination of alkynes involves very hazardous or inconvenient r ...

2022

Carbon K-edge x-ray emission spectroscopy of gas phase ethylenic molecules

Majed Chergui, Camila Bacellar Cases Da Silveira, Rebecca Ann Ingle, Luca Longetti, Thomas Roland Barillot

We report on the C K-edge x-ray absorption spectra and the resonant (RXES) and non-resonant (NXES) x-ray emission spectra of ethylene, allene and butadiene in the gas phase. The RXES and NXES show clear differences for the different molecules. Overall both ...

IOP Publishing Ltd2022

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Alkyne

Synthesis, isolation and application of a sila-ketenyl anion

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

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

Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Carbon K-edge x-ray emission spectroscopy of gas phase ethylenic molecules

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Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones

Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes

Synthesis and Applications of Ynimines and Enantioselective Total Synthesis of Artatrovirenol A

Synthesis, isolation and application of a sila-ketenyl anion

Radical Alkynylations with EthynylBenziodoXolones: From Photocatalysis to Direct Excitation

Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation

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

Carbon K-edge x-ray emission spectroscopy of gas phase ethylenic molecules