Publications associées à Metal–halogen exchange

Methods for high-throughput synthesis and screening of peptide libraries

Macrocycles provide an attractive modality for drug development but the identification of ligands to targets of interest is hindered by the lack of large macrocyclic compound libraries for high-throughput screening. A strategy to efficiently synthesize lar ...

EPFL2024

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

Structure 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 ...

2021

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

Remote C(sp(3))-H Arylation and Vinylation of N-Alkoxypyridinium Salts to delta-Aryl and delta-Vinyl Alcohols

Qian Wang, Jieping Zhu, Xu Bao

The reaction of readily available and bench-stable N-alkoxypyridinium salts with arylboronic and vinylboronic acids afforded delta-aryl and delta-vinyl alcohols, respectively, in the presence of fac-Ir(ppy)(3) and Cu(OTf)(2) dual catalysts. The reaction ta ...

WILEY-V C H VERLAG GMBH2019

Decarboxylative C(sp3)–N cross-coupling via synergetic photoredox and copper catalysis

Xile Hu, Runze Mao, Jonathan Balon, Adrian Frey

Amines are a quintessential moiety in bioactive molecules, pharmaceuticals and organic materials. Transition-metal-catalysed C–N coupling of aryl electrophiles has been established as a powerful and reliable method for amine synthesis. However, the analogo ...

2018

Stereoselective synthesis of alkenes via base-metal-catalyzed addition reactions to alkynes and activation of hydrogen peroxide and carbon dioxide by iron complexes

Fedor Zhurkin

Alkene functionality can be found in the majority of natural products, drugs, catalysts and organic materials. Therefore, methods of C-C double bond formation constitute a cornerstone of organic synthesis. Selective formation of either (Z)- or (E)-isomer i ...

EPFL2017

Implementation and Characterization of Dynamic Genetic Networks in Vitro

Henrike Marie Niederholtmeyer

Transcription and translation (TX-TL) can be performed in vitro, outside of cells, allowing the assembly and analysis of genetic networks. This approach to engineering biological networks in a less complex and more controllable environment could one day al ...

EPFL2015

Implementation of cell-free biological networks at steady state

Sebastian Maerkl, Henrike Marie Niederholtmeyer, Viktoria Stepanova

Living cells maintain a steady state of biochemical reaction rates by exchanging energy and matter with the environment. These exchanges usually do not occur in in vitro systems, which consequently go to chemical equilibrium. This in turn has severely cons ...

National Academy of Sciences2013

Intricacies of Describing Weak Interactions involving Halogen Atoms within Density Functional Theory

Ursula Röthlisberger, Ivano Tavernelli, Manuel Dömer

In this work we assess the performance of different dispersion-corrected DFT approaches (M06, M06-2X, DFT-D3 and DCACP) in reproducing high-level wave function based benchmark calculations on the weakly bound halogen dimers (X2)2 and X2-Ar (for X=F,Cl,Br,I ...

Amer Chemical Soc2013

Influence of Halogen Atoms on a Homologous Series of Bis-Cyclometalated Iridium(III) Complexes

Michael Graetzel, Mohammad Khaja Nazeeruddin, Rosario Scopelliti, Ursula Röthlisberger, Ivano Tavernelli, Basile Curchod, Frédéric Steimer

A series of homologous bis-cyclometalated iridium(III) complexes Ir(2,4-di-X-phenyl-pyridine)2(picolinate) (X = H, F, Cl, Br) HIrPic, FIrPic, ClIrPic, and BrIrPic has been synthesized and characterized by NMR, X-ray crystallography, UV–vis absorption and e ...

2012

Creating Tertiary and Quaternary Carbon Centers by Nickel and Copper-Catalyzed Cross-Coupling Reactions of Alkyl Electrophiles

Peng Ren

Transition-metal-catalyzed C-C coupling reactions have been extensively studied in the past three decades. These reactions have become invaluable to fundamental research and industrial applications, because they can be used construct complicated molecules ...

EPFL2012

Copper-catalyzed cross coupling of functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents

Xile Hu, Lucas-Alexandre Stern, Peng Ren

A copper-based method is highly efficient for the cross-coupling of alkyl electrophiles with secondary and tertiary alkyl Grignard reagents. The method is distinguished by its broad substrate scope and high functional group tolerance. ...

Wiley-VCH Verlag GmbH2012

Di-n-butyltin(IV)-catalyzed dimethyl carbonate synthesis from carbon dioxide and methanol: An in situ high pressure 119Sn{1H} NMR spectroscopic study

Gabor Laurenczy

The reactivity of five di-n-butyltin(IV) complexes, n-Bu2Sn(OR)(2) (1), n-Bu2SnO (3), n-Bu2Sn(OR)O (4), (n-Bu2SnO)(2)(CO2) (6) and (n-Bu2SnO)(6)(n-Bu2SnOR)(2)(CO3) (7) (R = CH3), with CO2, suggested as possible catalyst precursors and key-interme ...

Elsevier2011

Highly selective additions of hydride and organolithium nucleophiles to helical carbenium ions

Philip Pattison, Jérôme Lacour

Unsymmetrical cationic [4] helicenes react with hydride or organolithium reagents and the two diastereotopic faces can be discriminated with high efficiency (dr up to and higher than 49 : 1) ...

2011

Functional group tolerant Kumada-Corriu-Tamao coupling of non-activated alkyl halides with aryl and heteroaryl nucleophiles: Catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents

Xile Hu, Oleg Vechorkin, Valérie Proust

A nickel(II) pincer complex [(MeNN2)NiCl] (1) catalyzes Kumada−Corriu−Tamao cross coupling of nonactivated alkyl halides with aryl and heteroaryl Grignard reagents. The coupling of octyl bromide with phenylmagnesium chloride was used as a test reaction. Us ...

2009

Solvent-enhanced coupling of sterically hindered reagents and aryl chlorides using functionalized ionic liquids

Paul Joseph Dyson, Zhaofu Fei, Ning Yan, Yuehui Li, Xuemei Yang

A highly efficient and poison-resistant system for the Suzuki coupling reaction based on hydroxyl-functionalized ionic liq. solvents has been established. Coupling of RC6H4X (X = Br, I, Cl) and 2-bromothiophene with R1C6H4B(OH)2 in 2-hydroxyethyl-substitut ...

2009

Preparation of asymmetrically substituted biaryldiphosphines as ligands for enantioselective hydrogenation

Provided is a process for prepn. of asym. substituted biaryldiphosphine ligands I (R1 = C1-6-alkyl, C3-10-cycloalkyl optionally substituted with one or more halogen atoms; R2, R3 = aryl, C5-10-cycloalkyl, C1-6-alkyl, or R2 = C5-10-cycloalkyl, C1-6-alkyl; R ...

(Lonza AG, Switz.).2006

Preparation of asymmetrically substituted biaryldiphosphines and their use as cocatalysts for transition metal catalyzed enantioselective hydrogenation

Asym. substituted biaryldiphosphine ligands I (R1 = C1-6-alkyl or C3-10-cycloalkyl optionally substituted with one or more halogen atoms; R2 and R3 are equal and are C5-10-cycloalkyl or C1-6-alkyl, or R2 is C5-10-cycloalkyl or C1-6-alkyl, and R3 is aryl op ...

(Lonza AG, Switz.).2006

Metal-bearing and trifluoromethyl-substituted pyrimidines: generation and functionalization

Levente Ondi

5-Pyrimidyllithium species are fairly stable when the metal is flanked by two electron-withdrawing substituents such as trifluoromethyl and chlorine or bromine. Thus, the corresponding 5-carboxylic acids are produced in high yields from 4,5-dibromo-6-(trif ...

2006