Article
Chemistry, Physical
Alexis Mifleur, Isabelle Suisse, Andre Mortreux, Mathieu Sauthier
Summary: The enantioselective hydroalkoxylation of butadiene with ethanol was achieved in the presence of nickel-based catalysts and chiral diphosphine ligands. Atropoisomeric chiral ligands like Segphos could yield Ee's up to 77%. Kinetics parameters were determined using a qualitative kinetic model, providing a better understanding of isomerization and racemization processes during the reaction.
Article
Chemistry, Multidisciplinary
Mingxin Liu, Nguyen Le, Christopher Uyeda
Summary: Nickel catalysts promote nucleophilic cyclopropanation reactions using CH2Cl2 as a methylene source and Mn as a stoichiometric reductant. The substrate scope includes a broad range of alkenes bearing electron-withdrawing substituents, and enantioselective cyclopropanations have been developed using chiral PyBox ligands. Mechanistic studies suggest the intermediacy of a (PyBox)Ni=CH2 species and DFT models provide a rationale for the nucleophilic character of the nickel carbene and the sense of enantioinduction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mateusz Janeta, Julius X. Heidlas, Olafs Daugulis, Maurice Brookhart
Summary: The reactivity of Ni-II and Pd-II olefin polymerization catalysts can be enhanced by introducing electron-withdrawing substituents on the supporting ligands, as demonstrated in this paper. Compared to the trifluoromethyl group, the trippy substituent shows stronger electron-withdrawing ability, leading to better performance in catalytic turnover frequency and polymer molecular weight.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Akira Saito, Shinya Adachi, Naoya Kumagai, Masakatsu Shibasaki
Summary: The strategic use of a sterically demanding Ni-II pincer carbene complex has enabled high enantioselectivity in the direct catalytic asymmetric addition of acetonitrile to aldehydes, resulting in highly enantioenriched beta-hydroxynitriles. This highly atom-economical process offers a promising pathway for utilizing inexpensive acetonitrile as a C2 building block in practical synthetic toolbox for asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xinhang Zhang, Hanyang Sun, Changhong Han, He Wang, Junpeng Zhang, Di Zhang, Bin Lin, Huiming Hua, Maosheng Cheng, Yongxiang Liu
Summary: The asymmetric total synthesis of neobraclactone C was achieved for the first time using a convergent synthetic strategy, with the longest linear sequence of 22 steps from known materials. Key steps of the synthesis include a steric hindrance/hydrogen bond dual-controlled Heck arylation reaction for the construction of hemiketal and cis-alkenyl in one step, as well as a CeCl3-catalyzed tricycle formation.
Article
Chemistry, Physical
Shucheng Ma, Fangjie Li, Guisheng Zhang, Lei Shi, Xiaoming Wang
Summary: A nickel-catalyzed reaction has been developed for the synthesis of 1,4-difluoroalkylarylation products from 1,3-butadiene with easily accessible difluoroalkyl bromides and arylboronic acids. The involvement of a key alkyl radical in the catalysis was demonstrated by a radical clock experiment. The operational simplicity, excellent functional-group compatibility, and high efficiency of this three-component reaction make it highly promising for the cost-efficient synthesis of difluoroalkylated compounds.
Article
Chemistry, Multidisciplinary
Arnab K. Maity, Annah E. Kalb, Matthias Zeller, Christopher Uyeda
Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Julia C. Reisenbauer, Benjamin N. Bhawal, Nicola Jelmini, Bill Morandi
Summary: This article reports a method for hydrocyanation reactions of alkenes and alkynes using commercially available aliphatic nitriles as a substitute for toxic hydrogen cyanide (HCN). The reaction employs a catalytic amount of inexpensive and stable NiCl2 along with a cocatalyst. The scalability and robustness of this method have been demonstrated.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Michiel T. Uiterweerd, Adriaan J. Minnaard
Summary: The first total synthesis of the complex rearranged angucyclinones Elmonin and Pratenone A is reported in this study. The key naphthalene fragment present in both targets was efficiently prepared using peri-directed C-H functionalization. Coupling with two anisole-derived fragments led to the synthesis of the natural products, with Elmonin being prepared using a biomimetic spiro-ketalization.
Article
Chemistry, Multidisciplinary
Xiaoqiang Hu, Xiaohui Kang, Zhongbao Jian
Summary: Living polymerization by suppressing chain transfer is a useful method for achieving precise control over molecular weight and structure. However, the suppression of chain transfer at high temperatures has been challenging in catalytic polymerization. In this study, the unprecedented living polymerization of ethylene at 130 degrees C is reported, with a narrow molecular weight distribution range of 1.04 to 1.08. Custom-designed alpha-diimine nickel catalysts play a key role in this breakthrough, remaining active even at 200 degrees C and enabling the formation of semi-crystalline, ultrahigh-molecular-weight polyethylene at 150 degrees C.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Wen-Bin Xie, Zhi Li
Summary: A series of chiral compounds were designed and synthesized for a highly enantioselective intramolecular hydroalkoxylation of nonactivated alkenes, resulting in the formation of 2-methylcoumarans with up to 99% yields and up to 97% enantiomeric excess under mild conditions.
Article
Chemistry, Physical
Qiankun Li, Chaoqun Wang, Hongliang Mu, Zhongbao Jian
Summary: This study presents a catalyst derived from cheap materials and short synthetic pathways that exhibits superior catalytic properties in olefin polymerization, enabling the formation of high molecular weight polyethylene.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Physical
Nicole S. Willeit, Wilhelm Klein, Peter Coburger, Elke Fritz-Langhals, Thomas F. Faessler
Summary: Single-site catalysis is an important strategy for optimizing heterogeneous catalytic reactions. A synthetic protocol for synthesizing four cluster compounds with transition metals embedded in a polyhedral cluster has been presented. The catalytic potential of the compounds has been investigated for various olefin isomerisation reactions. The results show that these single-site homogeneous catalysts can significantly increase the efficiency of catalysts and allow for sustainable use of expensive and less abundant transition metals.
Article
Chemistry, Multidisciplinary
Kouki Matsubara
Summary: The development of new N-heterocyclic carbene (NHC)-Ni complexes as catalysts has shown promising results, including the discovery of NHC-Ni(I) intermediates with excellent catalytic activity. Different types of Ni(I) complexes, such as dinuclear and mononuclear, have been identified as intermediates in these catalytic reactions, leading to a better understanding of the reaction mechanisms and potential prospects.
Article
Chemistry, Applied
Alexis Mifleur, Helene Ledru, Adrien Lopes, Isabelle Suisse, Andre Mortreux, Mathieu Sauthier
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Multidisciplinary
Mohammed Samir Ibn El Alami, Isabelle Suisse, Sami Fadlallah, Mathieu Sauthier, Marc Visseaux
COMPTES RENDUS CHIMIE
(2016)
Article
Chemistry, Organic
Remi Blieck, Mohamed Salah Azizi, Alexis Mifleur, Maxime Roger, Clement Persyn, Mathieu Sauthier, Helene Bonin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Mohamed Salah Azizi, Youssef Edder, Abdallah Karim, Mathieu Sauthier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Anna M. Maj, Svetlana Heyte, Marcia Araque, Franck Dumeignil, Sebastien Paul, Isabelle Suisse, Francine Agbossou-Niedercorn
Article
Chemistry, Inorganic & Nuclear
Anna M. Maj, Isabelle Suisse, Francine Agbossou-Niedercorn
TETRAHEDRON-ASYMMETRY
(2016)
Review
Chemistry, Multidisciplinary
C. Dussenne, T. Delaunay, V. Wiatz, H. Wyart, I. Suisse, M. Sauthier
Article
Chemistry, Physical
Alexis Mifleur, Delphine S. Merel, Andre Mortreux, Isabelle Suisse, Frederic Capet, Xavier Trivelli, Mathieu Sauthier, Smart A. Macgregor
Article
Chemistry, Physical
Alexis Mifleur, Andre Mortreux, Isabelle Suisse, Mathieu Sauthier
MOLECULAR CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Emma Wilson, Clement Dumont, Mathieu Drelon, Isabelle Suisse, Christophe Penverne, Mathieu Sauthier
Article
Crystallography
Yasmina Homrani, Abdelaziz Dahdouh, Mohamed Amin El Amrani, Pauline Loxq, Frederic Capet, Isabelle Suisse, Mathieu Sauthier
Summary: A dinuclear nickel complex with (S)-limonene based aminooxime ligand has been isolated and its crystal structure determined. The structure features two NiII ions coordinated in a distorted octahedral environment, with each oxime ligand forming two five-membered chelate rings. Numerous intermolecular and intramolecular hydrogen bonds in the crystal result in the formation of a three-dimensional network structure.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Leo Violet, Alexis Mifleur, Laurent Vanoye, Duc Hanh Nguyen, Alain Favre-Reguillon, Regis Philippe, Regis M. Gauvin, Pascal Fongarland
REACTION CHEMISTRY & ENGINEERING
(2019)
Article
Chemistry, Inorganic & Nuclear
Payel Laskar, Keishi Yamamoto, Anga Srinivas, Alexis Mifleur, Haruki Nagae, Hayato Tsurugi, Kazushi Mashima
DALTON TRANSACTIONS
(2017)
