Article
Chemistry, Multidisciplinary
Alexander Reichle, Magdalena Koch, Hannes Sterzel, Lea-Joy Grosskopf, Johannes Floss, Julia Rehbein, Oliver Reiser
Summary: The visible light-mediated copper-catalyzed vicinal difunctionalization of olefins utilizing bromonitroalkanes as ATRA reagents is reported. This method offers high yields, fast reaction times, and environmentally benign reaction conditions with a wide scope, allowing rapid functionalization of activated and unactivated olefins. Additionally, it demonstrates the late-stage functionalization of biologically active molecules and the upscaling to gram quantities, providing possibilities for further transformations such as the preparation of nitro- and aminocyclopropanes. Moreover, this study highlights the unique role of copper in photoredox catalysis by stabilizing and interacting with radical intermediates in its coordination sphere, as revealed by EPR studies that show its superior performance compared to iridium-based photocatalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Mummadi Sandeep, Bangarigalla Shantharjun, Geetala Pradeep Kumar, Kallu Rajender Reddy
Summary: A simple, mild, and efficient oxidative copper-catalyzed regioselective trifluoromethylation of imidazo[1,5-a]-N-heteroarenes has been developed. This method offers biologically relevant trifluoromethylated fused imidazoles in moderate to good yields with good functional group tolerance under mild conditions. Key features include short reaction time and room temperature reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhenhua Zhang, Julius B. Stueckrath, Stefan Grimme, Andreas Gansaeuer
Summary: Cp2Ti(TFA) is a versatile catalyst for the [2+2] cycloaddition of bisenones through inner-sphere electron transfer, with a unique 5-exo step as the rate-determining step followed by a favorable 4-exo cyclization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
James E. Baumann, Gojko Lalic
Summary: A new method for the differential dihydrofunctionalization of terminal alkynes has been developed, enabling the synthesis of allylic boronate esters through a reductive three-component coupling reaction. This transformation, promoted by a copper/palladium catalyst system, hydrofunctionalizes both pi-bonds of the alkyne. The method is compatible with a wide range of functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Arghya Banerjee, Satavisha Sarkar, Jagrut A. Shah, Nicoline C. Frederiks, Emmanuel A. Bazan-Bergamino, Christopher J. Johnson, Ming-Yu Ngai
Summary: The study presents a visible-light-induced copper catalysis for the production of diverse heterocycles, with high tolerance to various functional groups. Preliminary mechanistic investigation suggests a cooperative action of two catalysts under visible-light irradiation to facilitate the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Article
Chemistry, Multidisciplinary
Kun Guo, Arjan W. Kleij
Summary: A mild copper-mediated protocol has been developed for borylation of alkynyl cyclic carbonates, yielding either stereoselective diborylation of the propargylic surrogate or traceless monoborylation depending on the reaction partner. Control experiments have shown that a small change in the diboron(4) reagent can lead to competitive alcohol-assisted protodemetalation, resulting in the formation of alpha-hydroxyallene products under ambient conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sachini Rodrigo, Atanu Hazra, Jyoti P. Mahajan, Hien M. Nguyen, Long Luo
Summary: AC electrolysis can overcome functional group compatibility limitations and enable sequential addition of two functional groups. Cyclic voltammetry studies indicate that product yields are influenced by the regeneration of starting materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Nagarajan Ramkumar, Larisa Baumane, Dzintars Zacs, Janis Veliks
Summary: A simple process for the oxy-monofluoromethylation of alkenes is presented. The use of visible-light copper(I) photoredox catalysis, in combination with an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands, enables the synthesis of gamma-fluoro-acetates from various olefinic substrates under mild conditions. The study also demonstrates its applications in late-stage diversification of complex molecules, amino acids, and the synthesis of fluoromethylated heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Lindie Marais, Hermanus C. M. Vosloo, Andrew J. Swarts
Summary: Oxidative transformations involve converting organic substrates into oxygenates for pharmaceutical and chemistry industries. The mechanistic pathways of Cu-based catalyst systems include the initial oxidation state of copper, the redox lability of these oxidation states and the nature of the Cu-based active species.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Physical
Tamara Jurado-Vazquez, Efren Rosaldo, Alma Arevalo, Juventino J. Garcia
Summary: This paper reports a homogeneous copper-based catalyst that can catalyze the hydrogenation reaction of levulinic acid under mild reaction conditions, with high yield and selectivity.
Article
Chemistry, Organic
Lorenzo Poletti, Alessandro Massi, Daniele Ragno, Federico Droghetti, Mirco Natali, Carmela De Risi, Olga Bortolini, Graziano Di Carmine
Summary: Here, we present the α-selective Giese reaction between pyranosyl/furanosyl bromides and dehydroalanine analogues, which enables the synthesis of highly valuable α-C-glycosyl alanines through photocatalysis. The reactions achieve up to 99% yield of the desired products when using diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HE) as an additive. Both protocols use N,N-diisopropylethylamine (DIPEA) as a reductant. A mechanistic study using transient absorption spectroscopy reveals a halogen-atom transfer (XAT) process in C-glycosyl radical formation.
Article
Chemistry, Organic
Vera A. Vil', Valentina M. Merkulova, Alexey I. Ilovaisky, Stanislav A. Paveliev, Gennady Nikishin, Alexander O. Terent'ev
Summary: Fluorinated ketones were synthesized via electrochemical method in an undivided cell, with yields ranging from 20% to 85%.
Article
Chemistry, Multidisciplinary
Debasish Mandal, Suman Maji, Tanay Pal, Soumya Kumar Sinha, Debabrata Maiti
Summary: This review provides a comprehensive overview of the transition metal-mediated construction of C(sp(3), sp(2), and sp)-CF3 bonds in aliphatic and aromatic hydrocarbons. It discusses various trifluoromethylating agents and their mechanisms. This review is of great significance for further development in trifluoromethylation reactions and agrochemical drugs.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ling Dai, Ying-Ying Chen, Li-Jun Xiao, Qi-Lin Zhou
Summary: Intramolecular enantioselective radical C(sp(3))-H functionalization allows for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp(3))-H amination remain elusive. Here, a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp(3))-H amination with peroxide as an oxidant is reported. This method allows for the transformation of various alkylarenes and amides into chiral amines with high enantioselectivities and has good functional group tolerance and broad substrate scope. Moreover, it can be used to synthesize bioactive molecules, including chiral drugs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Xiao-Nan Zhang, Gen-Qiang Chen, Xiang Dong, Yin Wei, Min Shi
ADVANCED SYNTHESIS & CATALYSIS
(2013)
Review
Chemistry, Multidisciplinary
Wei Yuan, Xiang Dong, Yin Wei, Min Shi
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Organic
Qing-An Chen, Xiang Dong, Mu-Wang Chen, Duo-Sheng Wang, Yong-Gui Zhou, Yu-Xue Li
Article
Chemistry, Organic
Wei Yuan, Xiang Dong, Min Shi, Patrick McDowell, Guigen Li
Article
Chemistry, Organic
Xiao-Nan Zhang, Xiang Dong, Yin Wei, Min Shi
Article
Chemistry, Multidisciplinary
Mengqi Shen, Chao Yu, Huanqin Guan, Xiang Dong, Cooro Harris, Zhen Xiao, Zhouyang Yin, Michelle Muzzio, Honghong Lin, Jerome R. Robinson, Vicki L. Colvin, Shouheng Sun
Summary: Nanoparticle catalysts show promise in enabling multistep chemical reactions in a tandem fashion for green chemistry synthesis. Specifically, AuPd alloy NPs exhibit excellent catalytic performance in one-pot reactions to produce high-quality PBO, while Cu NPs can catalyze similar reactions to form PBO when formic acid is replaced.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Xiang Dong, Alexander M. Brown, Audra J. Woodside, Jerome R. Robinson
Summary: Experiments and computations have shown that N-oxides can greatly enhance the performance of a lanthanum aminobisphenolate catalyst in the ring-opening polymerization. It was found that donor electronics control the catalyst activity, while donor sterics control catalyst deactivation.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Xiang Dong, Jerome R. Robinson
Summary: This perspective article discusses the versatile roles of neutral donor ligands in modulating catalyst performance in the ring-opening polymerization (ROP) of cyclic esters. It identifies unifying concepts and trends that emerge across various catalyst systems, donor ligands, and cyclic esters, and highlights the importance of design strategies, bonding preferences, and mechanisms of action in solidifying relationships between catalyst structure and function for the synthesis of sustainable polymers.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiang Dong, Jerome R. Robinson
