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Development of remote C-H bond functionalization of redox-active alcohol derivatives and oxidative transformations under photoredox catalysis

Publications associées (91)

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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

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

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

Head‐to‐Tail Dimerization of N‐Heterocyclic Diazoolefins

Rosario Scopelliti, Kay Severin, Farzaneh Fadaei Tirani, Andrzej Sienkiewicz, Tak Hin Wong, Zhaowen Dong, Paul Varava, Anastasia Gitlina, Wolfram Feuerstein

The head-to-tail dimerization of N-heterocyclic diazoolefins is described. The products of these formal (3+3) cycloaddition reactions are strongly reducing quinoidal tetrazines. Oxidation of the tetrazines occurs in a stepwise fashion, and we were able to ...

2023

Terminal 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 GMBH2023

Rh-catalyzed C-H Bond Heteroarylation with Hypervalent Iodine Reagents and Pd-Catalyzed Tethered Functionalizations of Carbon-Carbon Multiple Bonds.

Ashis Kumar Das

Transition metal-catalyzed C-H activation is a powerful tool for the synthesis of organic building blocks, materials, and natural products. Over the last decade, directing-group-assisted metal-catalyzed C-H functionalization has attracted increasing intere ...

EPFL2022

Highly Ordered and Thermally Stable FeRh Cluster Superlattice on Graphene for Low-Temperature Catalytic CO Oxidation

Harald Brune, Jean-Guillaume De Groot, Hao Yin

We report on bimetallic FeRh clusters with a narrow size-distribution grown on graphene on Ir(111) as a carbon-supported model catalyst to promote low-temperature catalytic CO oxidation. By combining scanning tunneling microscopy with catalytic performance ...

WILEY-V C H VERLAG GMBH2022

Activation of aminocyclopropanes via radical intermediates

Jérôme Waser, Mingming Wang

Aminocyclopropanes are versatile building blocks for accessing high value-added nitrogen-containing products. To control ring-opening promoted by ring strain, the Lewis acid activation of donor-acceptor substituted systems is now well established. Over the ...

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

Atomic Level Insights of Non-Noble Metal Catalysts for the Oxygen Evolution Reaction

Lichen Bai

The conversion of intermittent renewable energy resources in the form of chemical bond, such as hydrogen production from electrochemical water splitting, is a promising way to satisfy the future global energy demand and address the environmental issues. Th ...

EPFL2021