Article
Chemistry, Organic
Yiyang Zhang, Hong Sun, Ying Chen, Yaocheng Shi, Lei Yu
Summary: In this paper, it was discovered that a polyaniline-supported tungsten catalyst could efficiently catalyze the alpha-H alkylation reaction of ketone with alcohol, producing only water as the byproduct. The reaction occurred under mild conditions, with a wide substrate scope, and demonstrated strong production capacity.
Article
Polymer Science
Kosuke Isaji, Shin-ichi Matsuoka, Masato Suzuki
Summary: A new copolymer of NB with exo-NBL was successfully synthesized using Pd catalytic systems, leading to a polymer with improved solubility in chlorinated solvents and high thermal stability. This copolymer showed a random sequence and enhanced physical properties compared to poly(NB).
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Multidisciplinary Sciences
Eiji Shirakawa, Yuki Ota, Kyohei Yonekura, Keisho Okura, Sahiro Mizusawa, Sujan Kumar Sarkar, Manabu Abe
Summary: An electron has been found to catalyze the cross-coupling reaction of organometallic compounds with aryl halides, which is more desirable for green and sustainable chemistry compared to transition metal catalysis. However, high temperature is required for this electron catalysis. We discovered that visible light photoirradiation can accelerate the electron-catalyzed reaction by using photoredox catalysis, enabling the reaction to proceed at room temperature. The supply of the electron catalyst through photoredox catalysis also expands the scope of aryl halides.
Article
Chemistry, Physical
Han-Jun Ai, Fengqian Zhao, Hui-Qing Geng, Xiao-Feng Wu
Summary: The letter discusses a generic method for the synthesis of linear thioesters through palladium-catalyzed thiocarbonylation of alkenes. This approach allows for the straightforward production of desired thioesters from readily available alkenes with moderate to good yields.
Review
Chemistry, Applied
Christopher S. Horbaczewskyj, Ian J. S. Fairlamb
Summary: This review analyzes the use of ppm level palladium concentrations in catalytic cross-coupling reactions and their relationship to mole percentage. It suggests that ppm level palladium could be a practical descriptor of catalyst quantities in palladium-catalyzed cross-coupling reactions. The study also compares palladium with other metal catalyst systems, providing insights into the spread of ppm palladium across various studies in cross-coupling chemistry literature.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Review
Chemistry, Inorganic & Nuclear
Tharique N. Ansari, Fabrice Gallou, Sachin Handa
Summary: In the last few decades, cross-coupling approaches using palladium as a catalyst have been widely used for efficient generation of structural diversity. However, traditional practices in organic synthesis have been found to be inefficient due to the use of organic solvents. Using water as a reaction medium along with non-ionic surfactants provides a sustainable alternative, reducing the reliance on toxic organic solvents. This review discusses recent advances in micellar catalysis applied to palladium-mediated cross-couplings, as well as future directions and challenges.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Rajesh Kancherla, Krishnamoorthy Muralirajan, Sayan Dutta, Kuntal Pal, Bo Li, Bholanath Maity, Luigi Cavallo, Magnus Rueping
Summary: The development of metal complexes that can function as both photocatalysts and cross-coupling catalysts is challenging. This study reports that divalent palladium can act as a light-absorbing species to achieve carbon-nitrogen cross-coupling reactions under air. Palladium acetate can be used as both the photocatalyst and cross-coupling catalyst for the selective cross-coupling amination of differently substituted aryl halides at room temperature.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Article
Multidisciplinary Sciences
Madeleine C. Deem, Joshua S. Derasp, Thomas C. Malig, Kea Legard, Curtis P. Berlinguette, Jason E. Hein
Summary: Ring walking in Buchwald-Hartwig amination reactions is influenced by the chelating nature of the ligand, while the resting state of the catalyst has no impact. The study also differentiates catalysts that undergo ring walking from diffusion-controlled coupling. The insights gained from this study were used to achieve the desymmetrization of a tetrabrominated precursor.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Lei Zhang, Wenbo Hu, Heng Li, Jicheng Shi, Bingxin Yuan
Summary: An easily made and highly efficient terphenylphosphine ligand, TXPhos, is developed and applied for Pd-catalyzed Suzuki-Miyaura coupling reactions in aqueous media at ppm level. The terphenyl skeleton of TXPhos provides high stability and reactivity by increasing steric bulkiness and enhancing Pd-arene interactions. The TXPhos palladacycle exhibits excellent product yield under air atmosphere and significantly shortens the reaction period to minutes under micellar conditions, with a TOF up to 40,000 s(-1).
Article
Environmental Sciences
Arash Maghami, Nooshin Gholipour-Zanjani, Farhad Khorasheh, Mehdi Arjmand
Summary: The study successfully detoxified PCBs-contaminated transformer oil using catalytic hydrodehalogenation method. By utilizing Pd/MWCNTs catalyst in the atmosphere of argon, the amount of hexa-chlorine homologues and long half-lives and bioaccumulative PCB congeners were significantly reduced. The optimal reaction condition with an efficiency of 96.67% was found to be 70 degrees C, with catalyst loading of 8 wt% and reaction time of 3.23 h.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2022)
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Hyungdo Cho, Hidehiro Suematsu, Paul H. Oyala, Jonas C. Peters, Gregory C. Fu
Summary: Transition-metal catalysis of substitution reactions of alkyl electrophiles by nitrogen nucleophiles is an important strategy for synthesizing higher-order amines and controlling their stereochemistry. This study reports the photo-induced enantioconvergent coupling of racemic tertiary alkyl electrophiles with aniline nucleophiles using a readily accessible chiral copper catalyst. The mechanism of this catalytic process has been elucidated using various tools, leading to the identification of key copper-based intermediates in the proposed cycle.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Danielle E. Fagnani, Ariana O. Hall, Danielle M. Zurcher, Kikelomo N. Sekoni, Brianna N. Barbu, Anne J. McNeil
JOURNAL OF CHEMICAL EDUCATION
(2020)
Article
Polymer Science
Danielle E. Fagnani, Jessica L. Tami, Graeme Copley, Mackenzie N. Clemons, Yutan D. Y. L. Getzler, Anne J. McNeil
Summary: There has been an increased focus on sustainable polymers in recent years, but less attention has been paid to the end-of-life fate of polymers. It is suggested to place more emphasis on chemical recycling to promote a closed-loop plastic economy, in order to keep us on the path to sustainability.
Article
Chemistry, Inorganic & Nuclear
Matthew D. Hannigan, Anne J. McNeil, Paul M. Zimmerman
Summary: Identifying intermediates in Ni-containing reactions is challenging due to the reactivity and sensitivity of Ni complexes. The J-coupling between P atoms, J(PP), is proposed as an indicator of the oxidation state of Ni, which is also affected by parameters such as linker length and ligand properties. Results show that JPP values can predict the oxidation state of Ni in bidentate phosphine complexes, with factors like Lewis acidity/basicity affecting J(PP) predictably.
INORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
P. Takunda Chazovachii, Madeline J. Somers, Michael T. Robo, Dimitris Collias, Martin James, E. Neil G. Marsh, Paul M. Zimmerman, Jose F. Alfaro, Anne J. McNeil
Summary: The study introduces an open-loop recycling method for superabsorbent polymers used in diapers and feminine hygiene products. By decrosslinking via hydrolysis, an optional chain-shortening step via sonication, and functionalizing via Fischer esterification, the resulting adhesives show superior performance in life cycle assessment compared to those derived from petroleum feedstocks.
NATURE COMMUNICATIONS
(2021)
Article
Materials Science, Multidisciplinary
Dukhan Kim, Emily A. Mueller, Da Seul Yang, Danielle E. Fagnani, Jinsang Kim, Anne J. McNeil
Summary: This study demonstrates that a single copolymer containing a conjugated poly(3-hexylthiophene) backbone and fullerene-functionalized side chains can serve as a general blend stabilizer, suppressing phase separation in multiple conjugated polymer/fullerene thin film blends as well as in a photovoltaic device.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Dukhan Kim, Melanie S. Sanford, Thomas P. Vaid, Anne J. McNeil
Summary: The nonaqueous redox-matched flow battery (RMFB) stores charge on redox-active moieties tethered to insoluble polymer beads, transferring charge between electrodes and beads via soluble mediators with matching redox potentials. This approach enables high energy density and prevents crossover of active material.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Editorial Material
Polymer Science
Danielle E. Fagnani, Coralie Jehanno, Haritz Sardon, Anne J. McNeil
MACROMOLECULAR RAPID COMMUNICATIONS
(2022)
Editorial Material
Chemistry, Multidisciplinary
LaShanda T. J. Korley, Anne J. McNeil, Geoffrey W. Coates
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Analytical
Ziying Lei, Jing Zhang, Emily A. Mueller, Yao Xiao, Katherine R. Kolozsvari, Anne J. McNeil, Mark M. Banaszak Holl, Andrew P. Ault
Summary: In this study, the Tg and composition of individual atmospheric particles were determined using NanoTA and AFM-PTIR techniques. The results showed intraparticle variation in chemical composition and Tg, which could potentially improve the modeling of aerosol impacts on clouds and climate.
ANALYTICAL CHEMISTRY
(2022)
Article
Polymer Science
Matthew D. Hannigan, Jessica L. Tami, Paul M. Zimmerman, Anne J. McNeil
Summary: Catalyst-transfer polymerization (CTP) is a method used to synthesize conjugated polymers. Previous studies suggested that Ni0 catalysts are trapped by highly electron-rich arenes, but this research provides evidence that the catalyst trap is likely a NiII complex formed through oxidative insertion of Ni0 into the C-S bonds of thieno[3,2-b]thiophene. This finding may have significance in understanding or enabling the CTP of other monomers with fused thiophenes.
Article
Chemistry, Multidisciplinary
Danielle E. Fagnani, Dukhan Kim, Sofia I. Camarero, Jose F. Alfaro, Anne J. McNeil
Summary: New approaches are needed to reduce and reuse plastic waste. This study shows that by using the HCl generated from PVC in a paired-electrolysis reaction to chlorinate arenes, PVC waste can be effectively utilized with a lower global warming potential compared to using HCl. This method may inspire other strategies for repurposing waste PVC and related polymers.
Article
Chemistry, Physical
Gloria D. De La Garza, Aman Preet Kaur, Ilya A. Shkrob, Lily A. Robertson, Susan A. Odom, Anne J. McNeil
Summary: In this study, s-tetrazine derivatives were prepared and evaluated for their electrochemical properties, solubility, and cycling stability in nonaqueous redox flow batteries. The highly soluble 3,6-dimethoxy-s-tetrazine was found to undergo a reversible one-electron reduction and exhibited long cycling stability.
JOURNAL OF MATERIALS CHEMISTRY A
(2022)
Article
Environmental Sciences
Justin T. Harris, Gloria D. de la Garza, Angela M. Devlin, Anne J. McNeil
Summary: Many municipalities in the United States are using adsorbents to remove PFASs from drinking water, but conventional ones are slow. Researchers have developed materials that can rapidly adsorb PFASs within seconds, with high removal efficiencies. Functionalized cellulose fibers show promise as a bio-sourced and biodegradable material for water treatment technologies.
Article
Engineering, Environmental
P. Takunda Chazovachii, Julie M. Rieland, Violet V. Sheffey, Timothy M. E. Jugovic, Paul M. Zimmerman, Omolola Eniola-Adefeso, Brian J. Love, Anne J. McNeil
Summary: Microplastic pollution is widespread and a major concern, but removing microplastics from water using adhesives shows promising results. This method can efficiently remove up to 99% of microplastics within 5 minutes, offering a potential solution for remediating microplastic pollution in aquatic environments.
ACS ES&T ENGINEERING
(2021)
Article
Polymer Science
Tomohiro Kubo, Morgan S. Young, Kendra D. Souther, Matthew D. Hannigan, Anne J. McNeil
Summary: The discovery of catalyst-transfer polymerization allows unprecedented control over the length and sequence of conjugated polymers. A new method for high yield synthesis of poly(3-hexylthiophene) without the need for an inert atmosphere has been developed, making the process more accessible to a broader range of researchers.
JOURNAL OF POLYMER SCIENCE
(2021)