Publications related to Organocopper chemistry

Biobased surfactant

Jeremy Luterbacher, Songlan Sun, Stefania Bertella, Anastasiia Komarova

The present invention relates to a compound of the general formula (I), (II) and (III), more specifically of formula (Ia), (Ib), (Ic)wherein R11 and R12 or R21 and R22 or R31 and R32 are both hydrogen or form together with CHR50 a cyclic moiety or one of R ...

2024

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

Biobased surfactant

Jeremy Luterbacher, Songlan Sun, Stefania Bertella, Anastasiia Komarova

The present invention relates to a compound of the general formula (I), and (II)wherein one of R11 and R12 is hydrogen and the other is -CH2-R70, and one of R13 and R14 is hydrogen and the other is -CH2-R71, or wherein one of R11 and R12 is hydrogen and th ...

2024

One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(i) precursors

Jérôme Waser, Xingyu Liu, Nieves Pilar Ramirez Hernandez, Tobias Michael Milzarek

Bis(trifluoromethylated)benziodoxoles (Bx) are broadly used cyclic hypervalent iodine reagents due to their stability and unique chemical properties. However, current methods to access them require several steps and long reaction times, making their synthe ...

Royal Society of Chemistry2023

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 ide ...

EPFL2023

Biobased surfactants

Jeremy Luterbacher, Songlan Sun, Stefania Bertella, Anastasiia Komarova

Compound of the general formula (Ia), (Ib) and (Ic) R50 and R60 are different form each other and are selected from the group consisting of -R70, -ZR70, -Z-OH, -Z-NH2, -Z-SH, -Z-OC(O)R70, -OC(O)R70, - COOH and its corresponding salts, -C(O)NH2, -C(O)NH-R70 ...

2023

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

Mischa Schüttel

Macrocycles have raised much interest in the pharmaceutical industry due to their ability to bind challenging targets while often still being able to cross membranes to reach intracellular proteins. However, the development of macrocyclic ligands to new di ...

EPFL2023

Photochemical 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

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

Green solvents for chemical reactions

Jeremy Luterbacher, Anastasiia Komarova

The present invention relates to Use of a compound of the general formula (I), (II), (III), (IV), (V) or (VI) wherein R1 and R1', R21 and R21', R31 and R31' are the same and are hydrogen, a linear or branched C1 to C18 alkyl, a linear or branched C2 to C18 ...

2022

Tandem effect of Ag@C@Cu catalysts enhances ethanol selectivity for electrochemical CO2 reduction in flow reactors

Andreas Züttel, Thi Ha My Pham, Cedric David Koolen, Wen Luo, Jie Zhang, Mo Li, Youngdon Ko, Liping Zhong

CO-selective metals (e.g., Ag) on Cu catalysts improve the selec-tivity of multi-carbon (C2+) products in electrochemical CO2 reduc-tion. However, the origin of the improvement remains unclear due to the convolution of tandem and interface effects. Here, A ...

ELSEVIER2022

Copper-catalyzed transformations of carboradicals generated by electrochemical and photochemical methods: oxidative amination and polyfluoroarylation

Xiangli Yi

Organic radicals are highly active species that can undergo various transformations. Electrochemistry and photochemistry are efficient methods for the generation of these species of high energy, through single electron transfer processes under mild conditi ...

EPFL2021

New Strategies for the Functionalization of Alkenes Exploiting Tethering Chemistry and Ring Strain

Bastian Antoine Rodolphe Claude Muriel

Amino alcohols, cyclopropanes and nitriles are privileged structural motifs found in the scaffold of natural products and bioactive compounds. In addition, they are versatile building blocks in organic chemistry. The development of new and increasingly eff ...

EPFL2021

New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds

Guillaume Dominique Pisella

The development of a sequential copper-catalyzed oxy-alkynylation/intramolecular [4+2] cycloaddition of allenes and arenes was investigated at first. This one-pot protocol allowed the construction of complex polycylic architectures with high efficiency fro ...

EPFL2021

Synthetic methodologies for C-C and C-N bond formation involving alkyl radicals

Guido Barzanò

C-C and C-N bonds are some of the most common structures in molecules ranging from drugs to catalysts and to food additives. Many coupling reactions were developed to form these types of bonds with excellent selectivity and good performance. Still, the syn ...

EPFL2020

Copper(I) Based Photoredox Chemistry

Murat Alkan

Photoredox catalysis has become a powerful tool for chemists. However, the reliance on expensive Ir and Ru based photoredox catalysts (PC) motivates research for more sustainable options. Copper complexes based on favorable photophysical properties, high a ...

EPFL2020

Arylsilylation of Electron-Deficient Alkenes via Cooperative Photoredox and Nickel Catalysis

Xile Hu, Zhikun Zhang

Carbosilylation of alkenes can be an efficient approach to the synthesis of organosilicon compounds. However, few general methods of carbosilylation are known. Here, we introduce a strategy for arylsilylation of electron deficient terminal alkenes by combi ...

2020

Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds

Jérôme Waser, Bastian Antoine Rodolphe Claude Muriel

We report herein a radical‐mediated amination of cyclopropenes. The transformation proceeds through a cleavage of the three‐membered ring after the addition of an azide radical on the strained double bond and leads to tetrasubstituted alkenyl nitrile deriv ...

Wiley-VCH Verlag GmbH2020

Catalytic and antibacterial properties of 3-dentate carboxamide Pd/Pt complexes obtained via a benign route

Kurt Schenk, Farzaneh Fadaei Tirani

The complexes Pd-II(qcq)(OAc) and Pt-II(qcq)Cl have been synthesized using environmentally benign synthesized ligands and characterized by elemental analyses: Fourier transform infrared spectroscopy, UV-visible spectroscopy, H-1 NMR spectroscopy, and X-ray ...

WILEY2020

Dual Photoredox/Copper Catalysis for the Remote C(sp3 )−H Functionalization of Alcohols and Alkyl Halides by N -Alkoxypyridinium Salts

Qian Wang, Xu Bao, Jieping Zhu

Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded d-azido, d-cyano, and d-thiocyanato alcohols in high yields. The reaction went through a domino proc ...

Wiley-VCH Verlag GmbH2019