Article
Chemistry, Multidisciplinary
Feriel Rekhroukh, Linxing Zhang, Richard Y. Kong, Andrew J. P. White, Mark R. Crimmin
Summary: This study reports the reactions of cyclopropenes with compounds containing Mg-Mg bonds, demonstrating a concerted and stereoselective mechanism of 1,2-dimagnesiation. The findings shed new light on the stereochemistry of reactions involving magnesium reagents.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Lorenzo Pontini, Jamie A. Leitch, Duncan L. Browne
Summary: This study presents a solvent-free method for synthesizing cyclopropanes via a ball-milling-enabled Simmons-Smith reaction. By utilizing mechanochemical techniques to activate zinc(0), this protocol, which is simple to operate under air, enables the synthesis of various cyclopropane structures and gram-scale production.
Article
Chemistry, Physical
Reinald Fischer, Helmar Goerls, Philipp Schueler, Regina Suxdorf, Matthias Westerhausen
Summary: This study examines the reaction between 1,4-dioxane and Grignard reagent, resulting in the formation of three magnesium compounds. Further reactions lead to the synthesis of two target compounds. The structures of these compounds were determined through X-ray crystal structure determinations.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Organic
Yihang Li, Jia Sheng Ng, Bin Wang, Shunsuke Chiba
Summary: A protocol for synthesizing alpha-alkynylnitrones from 1,3-enynes has been developed using MgH2 triggered hydromagnesiation. The resulting alpha-alkynylnitrones can serve as versatile precursors for constructing various nitrogen-containing compounds.
Article
Chemistry, Multidisciplinary
Yang Gao, Simin Yang, Minwei She, Jianhong Nie, Yanping Huo, Qian Chen, Xianwei Li, Xiao-Qiang Hu
Summary: We report a practical route for the synthesis of valuable 3-aryl anthranils from readily available anthranils and simple arenes using electrophilic aromatic substitution (EAS) strategy. The method shows good compatibility with a wide range of arenes and delivers various structurally diversified 3-aryl anthranils in good yields and high regioselectivity. The synthesized 3-aryl anthranils are proven to be a highly robust platform for accessing biologically active compounds, drug derivatives, and organic optoelectronic materials.
Article
Chemistry, Organic
Ikuya Fujii, Kazuhiko Semba, Yoshiaki Nakao
Summary: Rhodium-aluminum bimetallic complexes catalyze the Kumada-Tamao-Corriu (KTC) cross-coupling reaction using arylmagnesium compounds generated from corresponding aryl fluorides or chlorides. This method allows the challenging KTC coupling reaction to be carried out using aryl fluorides as nucleophiles, resulting in various biaryls.
Article
Chemistry, Organic
Tomoya Yokota, Hyuma Masu, Takayoshi Arai
Summary: This paper reports a chiral NCN-pincer Pd-OTf complex containing a chiral imidazolidine, which can promote the asymmetric nucleophilic addition of unprotected 2-vinylindoles to N-Boc imines in a Friedel-Crafts-type manner. The resulting (2-vinyl-1H-indol-3-yl)-methanamine products serve as versatile platforms for constructing multiple ring systems.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Quentin D. Tercenio, Erik J. Alexanian
Summary: The nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates reported in this study delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system, consisting of a simple nickel salt and a commercially available reductant, represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Article
Chemistry, Multidisciplinary
David Elorriaga, Felipe de la Cruz-Martinez, Maria Jesus Rodriguez-Alvarez, Agustin Lara-Sanchez, Jose Antonio Castro-Osma, Joaquin Garcia-Alvarez
Summary: The rapid addition of highly polar organometallic reagents to cyclic carbonates has been studied, allowing for the synthesis of highly substituted tertiary alcohols, beta-hydroxy esters, or symmetric ketones without the need for isolation or purification of any reaction intermediates.
Article
Multidisciplinary Sciences
Rina Takahashi, Anqi Hu, Pan Gao, Yunpeng Gao, Yadong Pang, Tamae Seo, Julong Jiang, Satoshi Maeda, Hikaru Takaya, Koji Kubota, Hajime Ito
Summary: This study presents a method for the general mechanochemical synthesis of magnesium-based carbon nucleophiles in air using a ball milling technique, which avoids the drawbacks of using dry organic solvents and long reaction times.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Alexander Kremsmair, Henrik R. Wilke, Matthias M. Simon, Quirin Schmidt, Konstantin Karaghiosoff, Paul Knochel
Summary: A general method for preparing enantiomerically and diastereomerically enriched secondary alkylmagnesium reagents was reported, which were used for highly stereoselective electrophilic aminations to produce alpha-chiral amines with up to 97% ee. The reaction involved the formation of optically enriched secondary mixed alkylmagnesium species, which were then reacted with electrophiles to yield alpha-chiral tertiary alcohols, ketones, amides, phosphines, and tertiary amines with yields of up to 89% and ee values of up to 99% over three reaction steps.
Review
Chemistry, Inorganic & Nuclear
Josef T. Boronski
Summary: The study of alkaline earth metal complexes is experiencing a renaissance, with stable molecular species featuring Mg-Mg bonds being extensively investigated. In addition to the species with Mg-Mg bonds, newly synthesized complexes with Be-Be and Ca-Ca bonds have also gained attention. These studies have revealed a richer and more complex chemistry of the group 2 metals than previously appreciated.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Dong Xia, Xin-Fang Duan
Summary: A new regiospecific alkylative/alkenylative cascade annulation of pyridines has been achieved, providing a novel approach to synthesizing azaindenones and related compounds. The long-standing issue of C2/C4 regioselectivity of pyridines has been effectively addressed in this protocol.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Francisco Foubelo, Miguel Yus
Summary: This report comprehensively describes the reactions of chiral N-tert-butylsulfinyl imines with various organometallic reagents, which can be applied in the synthesis of organic nitrogenated molecules, especially in the field of alkaloid compounds.
Editorial Material
Chemistry, Organic
Ruben Martin, Gary A. Molander
Summary: Ruben Martin and Gary A. Molander, renowned professors in the field of chemistry from Spain and the United States, respectively, have conducted in-depth research in their respective fields, focusing on developing new synthetic methods and catalytic reactions to provide important technological support for the preparation of high-value compounds.