Publications related to Aryl halide

Synthetic Receptors with Micromolar Affinity for Chloride in Water

Kay Severin, Farzaneh Fadaei Tirani, Damien Wen Chen, Cesare Berton, Sylvain Alexandre Marie Sudan

A water-soluble coordination cage was obtained by reaction of Pd(NO3)2 with a 1,3-di(pyridin-3-yl)benzene ligand featuring a short PEG chain. The cavity of the metal-organic cage contains one nitrate anion, which is readily replaced by chloride. The appare ...

Wiley-VCH Verlag GmbH2023

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Xile Hu, Srikrishna Bera, Deyun Qian

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation metho ...

AMER CHEMICAL SOC2021

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles

Xile Hu, Lara Lavrencic, Runze Mao, Xiangli Yi

Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carbox ...

Wiley-VCH Verlag GmbH2021

1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids

Nicolai Cramer, John Henry Reed

The potent nucleophilicity and remarkably low basicity of 1,3,2- diazaphospholenes (DAPs) is exploited in a catalytic, metal-free 1,4-reduction of free ,-unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the car ...

Wiley-VCH Verlag2020

Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition

Xile Hu, Alexis Baptiste Cheseaux, Guido Barzanò

Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stere ...

2019

One-step access to N-enoxyimides by gold-catalysed addition of N-hydroxyimides to terminal alkynes

Nicolai Cramer, Coralie Danielle Annick Duchemin

N-Enoxyimides have become attractive substrates for novel catalytic transformations, yet their tedious multi-step synthesis hampers full exploitation of their synthetic potential. We report a gold(I)-catalyzed protocol to access N-enoxyimides from simple a ...

2019

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

Nickamine and Analogous Nickel Pincer Catalysts for Cross-Coupling of Alkyl Halides and Hydrosilylation of Alkenes

Xile Hu, Zhikun Zhang, Renyi Shi

CONSPECTUS: Ligand development plays an essential role in the advance of homogeneous catalysis. Tridentate, meridionally coordinating ligands, commonly termed pincer ligands, have been established as a privileged class of ligands in catalysis because they ...

2019

Stable perovskite solar cells using tin acetylacetonate based electron transporting layers

Mohammad Khaja Nazeeruddin, Emad Oveisi, Yi Zhang, Robin Humphry-Baker, Sanghyun Paek, Yonghui Lee, Kyung Taek Cho, Hiroyuki Kanda, Aron Joel Huckaba, Hobeom Kim, Mousa Abdulla M E Abuhelaiqa

Organic-inorganic lead halide perovskites with over 23% power conversion efficiency have attracted enormous academic and industrial attention due to their low-cost fabrication and high device performance. Self-passivated tin oxide as an electron transport ...

ROYAL SOC CHEMISTRY2019

Decarboxylative C(sp3 )−O Cross-Coupling

Xile Hu, Runze Mao, Jonathan Balon

Alkyl aryl ethers are an important class of compounds in medicinal and agricultural chemistry. Catalytic C(sp3)−O cross‐coupling of alkyl electrophiles with phenols is an unexplored disconnection strategy to the synthesis of alkyl aryl ethers, with the pot ...

Wiley-VCH Verlag GmbH2018

Catalyst design for the transformation of CO2 into value-added products

Felix Daniel Bobbink

The mass-utilization of fossil resources has led to a dramatic increase in carbon dioxide (CO2) production, most of which is released directly into the Earth's atmosphere, resulting in global warming. Efforts to contain CO2 emissions and to capture, store ...

EPFL2018

Designer Anhydride Clears the Path for Alkoxycarbonylations in Catellani Reactions

Nicolai Cramer

In this issue of Chem, Dong and colleagues show that an engineered mixed carboxylate carbonate anhydride serves as an electrophilic trap in palladium/norbornene-catalyzed double functionalization of aryl iodides, enabling the introduction of the synthetica ...

Cell Press2016

Synthesis of cyclic carbonates from diols and CO2 catalyzed by carbenes

Paul Joseph Dyson, Felix Daniel Bobbink, Martin Hulla, Shoubhik Das, Weronika Gruszka

The synthesis of cyclic carbonates from epoxides and CO2 is a well-established reaction, whereas the synthesis of cyclic carbonates from diols and CO2 is considerably more challenging, and few efficient catalysts are available. Here, we describe heterocycl ...

Royal Society of Chemistry2016

Catalytic Applications and Mechanistic Investigations of Iron Bis(oxazolinylphenyl)amino Pincer Complexes in Kumada Cross Coupling and Hydrosilylation Reactions

Gerald Bauer

The aim of the project was to investigate iron bis(oxazolinylphenyl)amino (bopa) pincer complexes as pre-catalysts in the enantioselective Kumada cross-coupling of non-activated alkyl halides with aryl Grignard reagents. From this preliminary cross-couplin ...

EPFL2015

Nickel-Catalyzed Direct Alkylation of Terminal Alkynes at Room Temperature: A Hemilabile Pincer Ligand Enhances Catalytic Activity

Rosario Scopelliti, Xile Hu, Peng Ren, Pablo Marcelo Perez Garcia

Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there ha ...

American Chemical Society2015

Cross-Coupling of Nonactivated Primary and Secondary Alkyl Halides with Aryl Grignard Reagents Catalyzed by Chiral Iron Pincer Complexes

Xile Hu, Chi Wai Cheung, Gerald Bauer

Iron(III) bisoxazolinylphenylamido (bopa) pincer complexes are efficient precatalysts for the cross-coupling of nonactivated primary and secondary alkyl halides with phenyl Grignard reagents. The reactions proceed at room temperature in moderate to excelle ...

Georg Thieme Verlag2015

Iron Pincer Complexes as Catalysts and Intermediates in Alkyl Aryl Kumada Coupling Reactions

Rosario Scopelliti, Xile Hu, Matthew Wodrich, Gerald Bauer

Iron-catalyzed alkylaryl Kumada coupling has developed into an efficient synthetic method, yet its mechanism remains vague. Here, we apply a bis(oxazolinylphenyl)amido pincer ligand (Bopa) to stabilize the catalytically active Fe center, resulting in isola ...

American Chemical Society2015

Suzuki-Miyaura Cross-Coupling Reactions of Unactivated Alkyl Halides Catalyzed by a Nickel Pincer Complex

Xile Hu, Thomas Clément Di Franco, Nicolas Francis Michel Boutin

A nickel(II) pincer complex, [((N2N)-N-Me)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane rea ...

Georg Thieme Verlag2013

Synthesis, Reactivity, and Catalytic Application of a Nickel Pincer Hydride Complex

Rosario Scopelliti, Xile Hu, Jan Breitenfeld

The nickel(II) hydride complex [(MeN2N)Ni-H] (2) was synthesized by the reaction of [(MeN2N)Ni-OMe] (6) with Ph2SiH2 and was characterized by NMR and IR spectroscopy as well as X-ray crystallography. 2 was unstable in solution, and it decomposed via two re ...

American Chemical Society2012

A Well-Defined Ni Pincer Catalyst for Cross Coupling of Non-Activated Alkyl Halides and Direct C-H Alkylation

Oleg Vechorkin

Carbon-carbon bond forming reactions are among the most important and useful methods for organic synthesis. During the last years, significant progress has been made in this field. Whereas many catalysts were developed for the coupling of aryl, alkenyl, an ...

EPFL2011