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Concept

Schmidt reaction

Publications associées (24)

Sustainable, recyclable and biodegradable castor oil-derived elastomers enabled by dynamic acetoacetyl formed amides

Youwei Ma

Developing sustainable, recyclable, and biodegradable elastomers with the mechanical properties comparable to commercial polymers presents a formidable challenge. To this end, we synthesize a kind of mechanically robust elastomers cross -linked by acetoace ...

Elsevier Science Sa2024

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

Enantioselective Total Synthesis of (+)-Stephadiamine

Qian Wang, Jieping Zhu, Guang Li, Baochao Yang

An asymmetric synthesis of (+)-stephadiamine has been accomplished featuring (a) an enantioselective dearomatizative Michael addition to generate a quaternary stereocenter; (b) a domino sequence involving reductive generation of nitrone from γ-nitro ketone ...

2023

Diamine Synthesis via the Nitrogen-Directed Azidation of sigma- and pi-C-C Bonds

Jérôme Waser, Mingming Wang

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. ...

2021

Palladium-Catalyzed Synthesis of Ketenimines from Isocyanides and Synthetic Studies Towards the Total Synthesis of Mersilongine

Mathias Mamboury

In the first chapter of this thesis, the development of two new reactions for the synthesis of vinyl ketenimines and alpha-oxo-ketenimines from isocyanides is presented. These palladium-catalyzed transformations both feature an isocyanide insertion / beta- ...

EPFL2019

α-Diimines as Versatile, Derivatizable Ligands in Ruthenium(II) p-Cymene Anticancer Complexes

Paul Joseph Dyson, Lucinda Kate Batchelor

α-Diimines are among the most robust and versatile ligands available in synthetic coordination chemistry, possessing finely tunable steric and electronic properties. A series of novel cationic ruthenium(II) p-cymene complexes bearing simple α-diimine ligan ...

2018

Palladium-Catalyzed Three-Component Reaction of Propargyl Carbonates, Isocyanides, and Alcohols or Water: Switchable Synthesis of Pyrroles and Its Bicyclic Analogues

Jieping Zhu, Qian Wang, Guanyinsheng Qiu

In the presence of a catalytic amount of Pd(OAc)2 and a stoichiometric amount of tert-butylamine, the reaction of propargyl carbonates, isocyanides, and alcohols afforded polysubstituted aminopyrroles in good yields. Using water as a nucleophile instead of ...

American Chemical Society2017

Morphology stabilization strategies for small-molecule bulk heterojunction photovoltaics

Kevin Sivula, Liang Yao, Xavier Adrian Jeanbourquin, Muhammad Aiman Bin Rahmanudin Hamdan, Arvindh Sekar, Emilie Aude Marie Ripaud

The greater crystallinity of solution-processed small-molecule organic semiconductors, compared to their polymer counterparts, renders the bulk heterojunction (BHJ) more susceptible to phase separation under thermal stress, decreasing device performance. H ...

Royal Society of Chemistry2017

Switchable [3+2] and [4+2] Heteroannulation of Primary Propargylamines with Isonitriles to Imidazoles and 1,6-Dihydropyrimidines: Catalyst Loading Enabled Reaction Divergence

Jieping Zhu, Qian Wang, Shuo Tong

Isonitrile 1 due to its carbene-like reactivity serves generally as a one-carbon synthon in a diverse set of organic transformations. We report in this article that the isocyano group can also act as a polarized triple bond to undergo, as a two-atom syntho ...

Wiley-Blackwell2016

(eta(6)-Arene) ruthenium complexes with P-coordinated phosphinoferrocene amides bearing extended polar substituents at the amide nitrogen: Synthesis, characterization and cytotoxicity

Paul Joseph Dyson, Tina Riedel

Heterobimetallic Ru-Fe complexes of the general formula [(eta(6)-p-cymene) RuCl2(Ph(2)PfcCONHCH(2)CH(2-)COY-kappa P)], where Y = Me, NH2, NHEt, NHPh, and NMe2, and fc = ferrocene-1,1'-diyl, were synthesized from p-cymene ruthenium dichloride dimer and phos ...

Elsevier Science Sa2016

Synthesis of Alkynylated Heterocycles by Direct C-H Alkynylation or Domino Alkynylation Reactions

Yifan Li

Heterocycles are important compounds in organic chemistry. To introduce functional groups on heterocycles or synthesize functionalized heterocycles stays a hot topic of research. Among all the functional groups, alkynes attracted a lot of attention not onl ...

EPFL2016

Cryogenic Spectroscopy and Quantum Molecular Dynamics Determine the Structure of Cyclic Intermediates Involved in Peptide Sequence Scrambling

Ursula Röthlisberger, Thomas Rizzo, Oleg Aseev

Collision-induced dissociation (CID) is a key technique used in mass spectrometry-based peptide sequencing. Collisionally activated peptides undergo statistical dissociation, forming a series of backbone fragment ions that reflect their amino acid (AA) seq ...

2015

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes

Jérôme Waser, Fides Benfatti, Florian Patrick Marie Daniel De la Barre De Nanteuil, Reto Frei, Filippo De Simone, Eloísa Sofía Serrano Robledo

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subcl ...

Royal Society of Chemistry2014

Stable Quasi-Solid-State Dye-Sensitized Solar Cells Using Novel Low Molecular Mass Organogelators and Room-Temperature Molten Salts

Michael Graetzel, Mohammad Khaja Nazeeruddin, Yong Ding, Bing Zhang, Chunyang Zhang, Li Tao

Stable quasi-solid-state dye-sensitized solar cells (DSCs) were fabricated by using room-temperature molten salts (1-methyl-3-hexyl-imidazolium iodide), and a series of diamine derivatives with different lengths of alkyl chain as low molecular mass organog ...

American Chemical Society2014

Zinc Bromide Promoted Coupling of Isonitriles with Carboxylic Acids To Form 2,4,5-Trisubstituted Oxazoles

Jieping Zhu, Qian Wang, Shuo Tong

Deviant behavior: In a deviation from “normal” reactivity, isocyanides underwent co-trimerization with carboxylic acids in the presence of ZnBr2 to smoothly provide oxazoles (see scheme). The reaction is thought to occur by initial nucleophilic addition of ...

Wiley-Blackwell2013

Amide Formation in One Pot from Carboxylic Acids and Amines via Carboxyl and Sulfinyl Mixed Anhydrides

Pierre Vogel, Dean Markovic

An efficient method has been developed for the preparation of yet unknown acyclic mixed anhydrides of carboxylic and sulfinic acids. Sterically hindered 2-methylbut-3-ene-2-sulfinyl carboxylates add primary and secondary amines preferentially onto the carb ...

Amer Chemical Soc2013

Self-Assembly of ß-Amyloid Peptides in Cells and on Solid Supports

Enrico Condemi

Neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease and Huntington's disease share common mechanisms characterized by protein misfolding and aggregation, including formation of plaques or inclusion bodies. The rapid growing number o ...

EPFL2011

Chemoselective C-H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C-C Cross-Coupling of Tertiary Amines with Terminal Alkynes. Reaction Scope and Mechanism

Pierre Vogel

FeCl2 catalyzes the oxidative C-C cross-coupling of tertiary amines with terminal alkynes into propargylamines using (t-BuO)2 as oxidant. The reaction can be applied to aromatic and aliphatic amines and alkynes without solvent. High chemoselectivity for am ...

2009

Nouvelles approches synthétiques de prodrogues de cyclosporine A et d'analogues antiviraux

Jérémy Bérard

The cyclosporins comprise a family of cyclic 11-peptides containing seven N-methylated, hydrophobic amino acids. Cyclosporine A (CsA) representing the major member of this family is widely used as immunosuppressive agent in organ transplantations. The biol ...

EPFL2008

Switch-peptides as folding precursors in self-assembling peptides and amyloid fibrillogenesis

Hilal Lashuel, Richard Alan Mimna, Karine Murat, Adrian Schmid, Marie-Stéphanie Camus, Jérémy Bérard

The study of conformational transitions of peptides has obtained considerable attention recently because of their importance as a mol. key event in a variety of degenerative diseases. However, the study of peptide self-assembly into beta-sheets and amyloid ...

2007