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A Well-Defined Ni Pincer Catalyst for Cross Coupling of Non-Activated Alkyl Halides and Direct C-H Alkylation

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Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts

Julien Aymeric Borrel

The alkyne motif is a versatile functional group often encountered in organic chemistry. It can be involved in various transformations such as the alkyne-azide cycloaddition and has found widespread application in medicinal chemistry, chemical biology and ...

EPFL2024

New Applications of 1,3,2-Diazaphospholenes in Catalysis

Johannes Klett

The constant urge to construct new molecules in an economical and sustainable fashion led to the development of numerous metal-catalyzed transformations. Organocatalysts consisting of abundant and more sustainable elements offer an elegant solution to over ...

EPFL2024

Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes

Jérôme Waser, Stefano Nicolai

Bicyclic carbocycles containing a high fraction of Csp3 have become highly attractive synthetic targets because of the multiple applications they have found in medicinal chemistry. The formal cycloaddition of bicyclobutanes (BCBs) with two- or three-atom p ...

Royal Soc Chemistry2024

Arylative Ring Expansion of 3-Vinylazetidin-3-Ols and 3-Vinyloxetan-3-Ols to Dihydrofurans by Dual Palladium and Acid Catalysis

Qian Wang, Jieping Zhu, Takuji Fujii

In contrast to the well-studied 1-vinylcyclobutanols, the reactivity of 3-vinylazetidin-3-ols 1 and 3-vinyloxetan-3-ols 2 under transition metal catalysis remains largely unexplored. We report herein their unique reactivity under dual palladium and acid ca ...

Wiley-V C H Verlag Gmbh2024

Editing Tetrasubstituted Carbon: Dual C–O Bond Functionalization of Tertiary Alcohols Enabled by Palladium-Based Dyotropic Rearrangement

Qian Wang, Jieping Zhu, Baochao Yang, Tristan Corentin Pierre Delcaillau

Many elegant asymmetric syntheses of enantioenriched tertiary alcohols have been developed, and both the transition metal-catalyzed and the radical-based peripheral functionalization of tertiary alcohols have attracted intensive research interest in recent ...

2024

Method for preparing an at least partially acetal-protected sugar

Jeremy Luterbacher, Songlan Sun, Lorenz Perry Manker, Anastasiia Komarova

The present invention relates to a method for preparing an at least partially acetal-protected sugar involving the step of reacting a sugar or a sugar derivative selected from the group consisting of an aldopentose, an aldohexose, an aldopentoside and an a ...

2024

Regiodivergent and Enantioselective Synthesis of Cyclic Sulfones via Ligand-Controlled Nickel-Catalyzed Hydroalkylation

Xile Hu, Chao Fan, Deyun Qian

Cyclic sulfones have demonstrated important applications in drug discovery. However, the catalytic and enantioselective synthesis of chiral cyclic sulfones remains challenging. Herein, we develop nickel-catalyzed regiodivergent and enantioselective hydroal ...

Wiley-V C H Verlag Gmbh2024

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 ...

EPFL2023

Development of Hetero-Vinylbenziodoxolone Reagents for Applications in Synthetic Methodology and Biomolecule Functionalization

Nina Declas

Among the numerous existing chemical motifs, alkenes, alkynes, enol ethers and enamides, with an unsaturated carbon-carbon bond, are versatile functional groups that are found in many natural products and bioactive compounds. They are widely used as valuab ...

EPFL2023

TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent

Dina Boyarskaya

Indole is one of the most important heterocycles widely present in bioactive natural products, pharmaceuticals, agrochemicals and materials. Being easily accessible, the 2-nitrostyrenes are attractive starting materials for the indole synthesis and the Cad ...

EPFL2023