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Concept

Organonickel chemistry

Related publications (12)

Terminal Alkynes as One-Carbon Donors in [5+1] Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B

Qian Wang, Jieping Zhu, Rémi Hugo Lavernhe

Transition-metal-catalyzed [4+2] heteroannulation of alpha,beta-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically su ...

Wiley-VCH Verlag GmbH2023

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

Access to Chiral Cyclopentane Scaffolds by Enantioselective Nickel-Catalyzed Annulations

Joachim Sven Ernst Ahlin

The cyclopentane scaffold has attracted much attention due to its ubiquity in numerous bioactive natural products such as prostaglandins and polyquinanes. However, despite a plethora of available procedures to access this motif, a lack of methods that riva ...

EPFL2016

From Dimethylamine to Pyrrolidine: The Development of an Improved Nickel Pincer Complex for Cross-Coupling of Nonactivated Secondary Alkyl Halides

Rosario Scopelliti, Xile Hu, Thomas Clément Di Franco, Pablo Marcelo Perez Garcia

Replacement of a dimethyl amino group of the amidobis(amine) nickel(II) pincer complex (1), [((N2N)-N-Me)-Ni-Cl], by a pyrrolidino group resulted in a new nickel(II) pincer complex (2), [((PNNN)-N-yr-N-Me)Ni-Cl]. Complex 2 is an efficient catalyst for Kuma ...

American Chemical Society2016

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

Xile Hu, Fang Song, Ivan Buslov

The first efficient and non-precious nanoparticle catalyst for alkene hydrosilylation with commercially relevant tertiary silanes has been developed. The nickel nanoparticle catalyst was prepared in situ from a simple nickel alkoxide precatalyst Ni((OBu)-B ...

Wiley-Blackwell2016

Nickel-catalyzed Hydrosilylation of Alkenes and Transition-Metal-Free Intermolecular α-C-H Amination of Ethers

Ivan Buslov

Transition-metal-catalyzed hydrosilylation of olefins is one of the most important methods for the preparation of organosilicon compounds, which have broad applications in both synthetic and material chemistry. For decades, precious metals, principally pla ...

EPFL2016

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

Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones

Nicolai Cramer, Pavel Alexandrovich Donets, Joachim Sven Ernst Ahlin

Cyclopentenones are versatile structural motifs of natural products as well as reactive synthetic intermediates. The nickel-catalyzed reductive [3+2] cycloaddition of alpha,beta-unsaturated aromatic esters and alkynes constitutes an efficient method for th ...

Wiley-Blackwell2014

Mechanistic Studies Related to Nickel-Catalyzed Alkyl-Alkyl Cross Coupling Reactions

Jan Breitenfeld

Cross-coupling reactions of non-activated alkyl halides are potentially useful chemical transformations. At the same time, however, they are challenging due to a series of unproductive side reactions. Recently, significant progress has been made to overcom ...

EPFL2013

Bimetallic Oxidative Addition Involving Radical Intermediates in Nickel-Catalyzed Alkyl-Alkyl Kumada Coupling Reactions

Xile Hu, Matthew Wodrich, Jan Breitenfeld, Jesus Ruiz

Many nickel-based catalysts have been reported for cross-coupling reactions of nonactivated alkyl halides. The mechanistic understanding of these reactions is still primitive. Here we report a mechanistic study of alkyl-alkyl Kumada coupling catalyzed by a ...

American Chemical Society2013

Nickel Complexes of a Pincer NN2 Ligand: Multiple Carbon-Chloride Activation of CH2Cl2 and CHCl3 Leads to Selective Carbon-Carbon Bond Formation

Rosario Scopelliti, Xile Hu, Oleg Vechorkin

A new pincer-type bis(amido)amine (NN2) ligand and its lithium and nickel complexes, including Ni(II) methyl, ethyl, and phenyl complexes, were synthesized. The Ni(II) alkyl complexes react cleanly with alkyl halides including chlorides to form C−C coupled ...

2008

Quantum calculations on the acid catalyzed rearrangements of norborn-5-en-2-one, 7-oxanorborn-5-en-2-one and 7-azanorborn-5-en-2-one - The electron-releasing effect of homoconjugated carbonyl group

Pierre Vogel

Protonation of norbom-5-en-2-one gives 6-oxo-2-norbomyl cation (2) as most stable C7H9O+ cation. Quantum calculations at B3LYP/6-31G(d) level (gas phase, 1 atm, 25 degrees C) predict a C-s-structure for 2 that can be represented as an intramolecular pi-com ...

2008