Publication
Development of Hetero-Vinylbenziodoxolone Reagents for Applications in Synthetic Methodology and Biomolecule Functionalization
Publications associées (94)
Novel Alkynylation Methods through the Combination of Hypervalent Iodine Reagents and Alkynyl-trifluoroborate Salts
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 ...
EPFL2024Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol ethers for the synthesis of bicyclo[4.1.1]octanes
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 Chemistry2024TiCl3-Mediated Reductive Cyclization of Tetrasubstituted Alkenes and Enol Esters Bearing a 2-Nitrophenyl Substituent
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 ...
EPFL2023Hypervalent Iodine: New Reagents and Functionalization of Peptides
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 ...
Synthesis of propargyl silanes from terminal alkynes via a migratory Sonogashira reaction
Jérôme Waser, Mikus Purins, Lucas Antoine Théo Eichenberger
Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an aryl-to-alkyl Pd-migration. Twenty-se ...
2023Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe
Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...
WILEY-V C H VERLAG GMBH2023Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling
Paul Joseph Dyson, Mingyang Liu
Efficient valorization of lignin, a sustainable source of functionalized aromatic products, would reduce dependence on fossil-derived feedstocks. Oxidative depolymerization is frequently applied to lignin to generate phenolic mono- mers. However, due to th ...
2023Recent progress in alkynylation with hypervalent iodine reagents
Jérôme Waser, Eliott Hugo Joran Le Du
Although alkynes are one of the smallest functional groups, they are among the most versatile building blocks for organic chemistry, with applications ranging from biochemistry to material sciences. Alkynylation reactions have traditionally relied on the u ...
ROYAL SOC CHEMISTRY2023Photocatalyzed [2σ + 2σ] and [2σ + 2π] Cycloadditions for the Synthesis of Bicyclo[3.1.1]heptanes and 5- or 6-Membered Carbocycles
Jérôme Waser, Matthew Wodrich, André Bossonnet
We report the use of photocatalysis for the homolytic ring-opening of carbonyl cyclopropanes. In contrast to previous studies, our approach does not require a metal cocatalyst or a strong reductant. The carbonyl cyclopropanes can be employed for both [2σ + ...
2023Photochemical 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