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Concept

Alpha-olefin

Publications associées (19)

Oxidative rearrangement of 1,1-disubstituted alkenes to ketones

Qian Wang, Jieping Zhu, Qiang Feng

The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a PdII/Pd0 catalytic cycle involving a b-hydride elimination step. This mechanistic scenario is inapplicable to ...

American Association for the Advancement of Science2023

Intermolecular oxidative amination of unactivated alkenes by dual photoredox and copper catalysis

Xile Hu, Xiangli Yi

Oxidative amination of alkenes via amidyl radical addition is potentially an efficient method to generate allylic amines, which are versatile synthetic intermediates to bioactive compounds and organic materials. Here by combining photochemical generation o ...

ROYAL SOC CHEMISTRY2021

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

Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

Jérôme Waser, Stefano Nicolai, Stephanie Grace Elizabeth Amos

We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolu ...

2020

Mechanistic Investigations of Nickamine-catalyzed Hydrosilylation of Alkenes: Nickel Nanoparticles Are the Active Species

Xile Hu, Marten Leendert Ploeger

Hydrosilylation is an important chemical process for the synthesis of organosilanes and for the production of silicone polymers. The wide variety of catalysts developed for this reaction generally follow a Chalk-Harrod, or a sigma-bond metathesis mechanism ...

SWISS CHEMICAL SOC2020

Mechanistic Studies of Two Ni-Catalyzed Reactions: Reductive Amidation of Esters with Nitroarenes and Hydrosilylation of Alkenes

Marten Leendert Ploeger

Mechanistic investigations into homogeneously catalyzed reactions are essential for the fur-ther development of synthetic methodologies. Insights in the overall reaction pathway and vital steps such as the rate-determining and selectivity-determining steps ...

EPFL2020

Palladium Catalysed Intramolecular Carbo-oxygenation of Propargylic Amines to Access 1,2-Amino Alcohols and alpha-Amino Ketones via in situ Tether Formation

Phillip Gulliver Dominic Greenwood

a-Amino ketones and 1,2-amino alcohols are important structural motifs in organic chemistry, that can be observed in natural products, pharmaceutically and bioactive compounds. For these reasons, they constitute privileged targets for the development of ne ...

EPFL2020

Cu Photoredox Catalysts Supported by a 4,6-Disubstituted 2,2 '-Bipyridine Ligand: Application in Chlorotrifluoromethylation of Alkenes

Xile Hu, Murat Alkan

Interest in base metal catalysis motivates the development of Cu-based photoredox catalysts for organic synthesis. However, only a few Cu catalysts have been applied in photoredox reactions, the majority of which contain one or two 1,10-phenanthroline liga ...

2018

Deactivation and Regeneration of Sulfonated Carbon Catalysts in Hydrothermal Reaction Environments

Oliver Kröcher, Frédéric Vogel

The deactivation pathways of sulfonated carbon catalysts prepared from different carbons were studied during the aqueous‐phase hydrolysis of cellobiose under continuous‐flow conditions. The sulfonation of carbon materials with a low degree of graphitizatio ...

2018

Predicting Product Distribution of Propene Dimerization in Nanoporous Materials

Berend Smit

In this work, a theoretical framework is developed to explain and predict changes in the product distribution of the propene dimerization reaction, which yields a mixture of C-6 olefin isomers, resulting from the use of different porous materials as cataly ...

American Chemical Society2017

In situ tether formation from amines and alcohols enabling highly selective Tsuji-Trost allylation and olefin functionalization

Jérôme Waser, Ugo Jonathan Orcel

The use of tethers allows to overcome reactivity and selectivity issues often encountered with intermolecular reactions. Although tethers have been successfully applied for decades, their installation and removal usually requires additional steps. This min ...

2017

Chemoselective Alkene Hydrosilylation Catalyzed by Nickel Pincer Complexes

Xile Hu, Mickael Montandon-Clerc, Ivan Buslov, Simona Mazza

Chemoselective hydrosilylation of functionalized alkenes is difficult to achieve using base-metal catalysts. Reported herein is that well-defined bis(amino) amide nickel pincer complexes are efficient catalysts for anti-Markovnikov hydrosilylation of termi ...

Wiley-Blackwell2015

Chemoselective Hydrogenation and Transfer Hydrogenation of Aldehydes Catalyzed by Iron(II) PONOP Pincer Complexes

Rosario Scopelliti, Xile Hu, Simona Mazza

Iron-catalyzed hydrogenation has drawn much attention, yet the scope and chemoselectivity of iron catalysis warrant further improvement. Here we report new iron pincer complexes as chemoselective hydrogenation and transfer hydrogenation catalysts. Several ...

American Chemical Society2015

Olefin Hydrogenation with Single-Site Gold

Butene hydrogenation activity is intimately connected with the occupied and unoccupied electronic states of gold active site. We prepare well-defined Au(III) sites in IRMOF-3 structure, and tuned the metal density-of-states by replacing the substituent gro ...

Polish Academy of Sciences Warsaw2014

Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines

Jérôme Waser, Stefano Nicolai

The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of a ...

American Chemical Society2011

Experimental and theoretical studies on the mechanism of hydrogenation by η6-arene β-diketiminato -ruthenium and -osmium complexes

Paul Joseph Dyson, Andrew Douglas Phillips

The β-diketiminate class of ligands is renowned for the stabilization of coordinatively unsatd. main-group and transition metal complexes. Moreover, the application and scope of transition metal β-diketiminate complexes in the catalytic transformation of o ...

2010

BCl3-Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

Pierre Vogel, Dean Markovic

The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO2 with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of ...

2010

Hydrocarboxylation of Terminal Alkenes in Supercritical Carbon Dioxide

Gabor Laurenczy

The catalytic hydrocarboxylation of linear alkenes to carboxylic acids using supercritical carbon dioxide as a solvent was studied. High selectivities in acids have been obtained. The best results were achieved when adding a perfluorinated surfactant to th ...

2008

Atom transfer radical additions with the cationic half-sandwich complex [Cp*Ru(PPh3)(2)(CH3CN)]OTf

Rosario Scopelliti, Kay Severin, Laurent Quebatte

The cationic ruthenium half-sandwich complex [CpRu(PPh3)(2)(CH3CN)][OTf] (2) (CP = eta(5)-C5Me5, OTf = SO3CF3) was synthesized by reduction of Cp*RuCl2 with zinc in the presence of NaOTf and subsequent reaction with PPh3. When NaOTf was omitted, the ...

2005