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Concept

Secondary (chemistry)

Related publications (23)

Role of Carbonyl Compounds for N-Nitrosamine Formation during Nitrosation: Kinetics and Mechanisms

Urs von Gunten, Florian Frédéric Vincent Breider, Yishuai Pan

N-Nitrosamines are potential human carcinogens frequently detected in natural and engineered aquatic systems. This study sheds light on the role of carbonyl compounds in the formation of N-nitrosamines by nitrosation of five secondary amines via different ...

2024

Solvent- and catalyst-free reduction of CO2 with ammonia borane

Andreas Züttel, Liping Zhong, Youngdon Ko

Ammonia borane (AB) has been extensively studied as a solid-state hydrogen storage material. On the other hand, its reactivity with CO2 is still unclear, especially in the solid state. By carefully controlling the CO2 pressure and temperature, AB efficient ...

Royal Soc Chemistry2024

Divergent Asymmetric Total Synthesis of (−)‐Voacafricines A and B

Qian Wang, Jieping Zhu, Rémi Julien Sylvain Andres

A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been accomplished featuring the following key steps: a)a catalyst-controlled asymmetric Pictet– Spengler reaction of 6-methoxytryptamine with a ch ...

Wiley-VCH Verlag GmbH2023

Reactions of amines with ozone and chlorine: Two novel oxidative methods to evaluate the N-DBP formation potential from dissolved organic nitrogen

Urs von Gunten, Karim-Alexandre Essaied

The composition of oxidant-reactive dissolved organic nitrogen (DON) is poorly characterized, although its ozonation is likely to form a great variety of disinfection by-products containing a nitrogen-oxygen bond (NDBPs). In this study, two chemical oxidat ...

PERGAMON-ELSEVIER SCIENCE LTD2022

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

Enhanced Treatment of Municipal Wastewater Effluents by Fe-TAML/H2O2: Efficiency of Micropollutant Abatement

Urs von Gunten

Combining iron with a tetraamido-macrocyclic ligand (Fe-TAML) as a catalyst and with hydrogen peroxide (H2O2) as the bulk oxidant is a process that has been suggested for the oxidative abatement of micropollutants during water treatment. In this study, the ...

AMER CHEMICAL SOC2021

Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes

Xile Hu, Chi Wai Cheung

Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamid ...

2018

Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes

Xile Hu, Chi Wai Cheung, Marten Leendert Ploeger

Transmidation is an attractive method for amide synthesis. However, transamidation of secondary amides is challenging. Here, we describe a reductive transamidation method that employs readily available nitro(hetero)arenes as the nitrogen sources, zinc or m ...

American Chemical Society2017

N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source

Paul Joseph Dyson, Felix Daniel Bobbink, Shoubhik Das

N-formylation and N-methylation of amines are important reactions that are used to produce a wide range of key intermediates and compounds. This protocol describes the environmentally benign N-formylation and N-methylation of primary and secondary amines u ...

Nature Publishing Group2017

A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions

Rosario Scopelliti, Xile Hu, Marko Stojanovic, Thomas Clément Di Franco

A new series of Ni NNN pincer complexes were synthesized and characterized. The main difference among these complexes is the substituents on the side arm amino group(s). No major structural difference was found except for the C-N-C angle of the various sub ...

Wiley-Blackwell2016

Suzuki-Miyaura cross-coupling of non-activated alkyl halides catalyzed by well-defined nickel pincer complexes

Thomas Clément Di Franco

Metal-catalyzed cross-coupling reactions are powerful and widespread methods for the carbon-carbon bond formation. Among the electrophile partners, non-activated alkyl halides remain challenging substrates because of their reluctance towards oxidative addi ...

EPFL2016

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

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

Synthesis and structure-activity studies of well-defined nickel complexes as catalysts for cross coupling of alkyl electrophiles

Pablo Marcelo Perez Garcia

This dissertation is devoted to the development of well-defined nickel complexes as catalysts for cross coupling processes of alkyl electrophiles. In chapter one, we summarize recent cross coupling methodologies of alkyl electrophiles using nickel based ca ...

EPFL2015

Amides in One Pot from Carboxylic Acids and Amines via Sulfinylamides

Pierre Vogel, Jianfei Bai

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2-ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic ...

Amer Chemical Soc2014

Mild and Phosphine-Free Iron-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides with Alkynyl Grignard Reagents

Xile Hu, Chi Wai Cheung, Peng Ren

A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to af ...

American Chemical Society2014

Copper-Catalyzed Alkylation of Benzoxazoles with Secondary Alkyl Halides

Rosario Scopelliti, Xile Hu, Peng Ren

Copper-catalyzed direct alkylation of benzoxazoles using nonactivated secondary alkyl halides has been developed. The best catalyst is a new copper(I) complex (1), and the reactions are promoted by bis[2-(N,N-dimethylamino)ethyl] ether. ...

American Chemical Society2012

A Structure-Activity Study of Ni-Catalyzed Alkyl-Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides

Rosario Scopelliti, Xile Hu, Oleg Vechorkin, Peng Ren, Kim Dimuth Von Allmen

A structure–activity study was carried out for Ni catalyzed alkyl–alkyl Kumada-type cross coupling reactions. A series of new nickel(II) complexes including those with tridentate pincer bis(amino)amide ligands (RN2N) and those with bidentate mixed amino-am ...

2011

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B-Alkylcatecholboranes

Philippe Renaud, Kurt Schenk

The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The su ...

2010

Micelles for delivery of nitric oxide

Jeffrey Alan Hubbell, Yun Suk Jo

Embodiments include a vehicle for delivery of nitric oxide comprising: a collection of micelles having an internal micelle core that comprises a polymer with N-diazeniumdiolate comprising NO complexed with secondary amines of the polymer. Embodiments inclu ...

2010