Publication
Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents
Related publications (56)
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 ...
EPFL2024Hypervalent 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 ...
Recent 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 CHEMISTRY2023Exploring 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 GMBH2022Radical 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 SOC2022Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations
Jérôme Waser, Julien Aymeric Borrel
Ethynylbenziodoxolones (EBXs) are commonly encountered reagents for the electrophilic alkynylation of nucleophiles. Herein, we report a one-pot, two-step process for EBX generation and their direct application in substrate functionalization. Our approach e ...
AMER CHEMICAL SOC2021Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents
Rosario Scopelliti, Jérôme Waser, Farzaneh Fadaei Tirani, Matthew Wodrich, Eliott Hugo Joran Le Du
Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis of ...
2021Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**
Jérôme Waser, Diana Cavalli, Franck Le Vaillant, Stephanie Grace Elizabeth Amos
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 ...
WILEY-V C H VERLAG GMBH2021Photochemical Functionalization of Heterocycles with EBX Reagents: C-H Alkynylation versus Deconstructive Ring Cleavage
Jérôme Waser, Marion Marie-Agnès Garreau
The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C-H functionalization of saturated O-heterocycles, as well as the deconstru ...
2020Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy-Allyl Cation Synthetic Equivalents
We report an Umpolung strategy of enol ethers to generate oxy-allyl cation equivalents based on the use of hypervalent iodine reagents. Under mild basic conditions, the addition of nucleophiles to aryloxy-substituted vinylbenziodoxolone (VBX) reagents, eas ...
WILEY-V C H VERLAG GMBH2020