Article
Chemistry, Organic
Qiao-Fei Bao, Ming Li, Yu Xia, Yu-Zhao Wang, Zhao-Zhao Zhou, Yong-Min Liang
Summary: The photocatalytic decarboxylative radical addition bifunctionalization cascade presented in this study relies on single-electron transfer to complete the catalytic cycle. The reaction offers advantages such as the use of commercially available materials, wide functional group compatibility, and mild conditions. Importantly, some amino acids and bioactive carboxylic acids can provide corresponding products in moderate to good yields, highlighting their potential value in drug development.
Article
Chemistry, Multidisciplinary
Dario Filippini, Mattia Silvi
Summary: The study presents a visible-light-mediated and transition metal-free olefination process using a defined alkene geometry to cross-couple complex molecular scaffolds containing carboxylic acids and aldehydes. By merging the Wittig reaction and photoredox catalysis, it enables rapid structural diversification of bioactive molecules and natural products with high functional group tolerance and the formation of a new alkene functional group with programmable E-Z stereochemistry.
Article
Chemistry, Applied
Nagarajan Ramkumar, Arturs Sperga, Sergey Belyakov, Anatoly Mishnev, Dzintars Zacs, Janis Veliks
Summary: Fluoroalkyl ethers have been extensively researched in the fields of pharmaceutical, agrochemical, nuclear imaging, and material sciences, leading to the development of new synthetic methods. Radical fluoroalkoxylation has emerged as a promising approach for synthesizing fluoroalkyl ethers. This study introduced a solid, easily accessible redox-active N-O reagent, 1-(fluoromethoxy)-3-methyl-benzotriazolium triflate (FMBT), which acts as a radical source of (mono)fluoromethoxy group under photocatalytic conditions. The synthetic potential of FMBT was demonstrated in the functionalization of olefins to obtain amino and ketomonofluoromethyl ethers, contributing to the study of chemical biology and drug discovery.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Applied
Jitender Singh, Anuj Sharma
Summary: Functionalized oxindoles are important heterocyclic structures found in many natural products and are key intermediates in drug synthesis. Visible light mediated methodologies for the synthesis of oxindoles have received significant attention and show promise for future applications.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Alexey A. Festa, Olga A. Storozhenko, Leonid G. Voskressensky, Erik V. van der Eycken
Summary: The use of visible light-promoted chemistry in halogenation and halofunctionalisation reactions has significant impact.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Organic
Ashish Kumar Sahoo, Amitava Rakshit, Anjali Dahiya, Avishek Pan, Bhisma K. Patel
Summary: An effective method for the green-light-induced synthesis of thio-functionalized pyrroles has been established, using beta-ketodinitriles and thiophenols as reactants and eosin Y as the photocatalyst. The study also demonstrates the scalability of the synthesis and introduces some useful synthetic modifications for the thio-functionalized pyrroles.
Article
Chemistry, Organic
Yan-Shun Zhang, Yin Wei, Min Shi
Summary: This study presents a sequential dual catalytic transformation for the rapid synthesis of polysubstituted caged oxa-bishomocubane products. The method is simple and utilizes readily available starting materials, providing good step-economy.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Qing-Yun Fang, Jie Han, Mingzhe Qin, Weipeng Li, Chengjian Zhu, Jin Xie
Summary: Reported here is a three-component 1,2-difunctionalization reaction of alkenes, unactivated alkyl bromides, and nucleophiles (e.g., amines and indoles) using a trinuclear gold catalyst [Au-3(tppm)(2)](OTf)(3). This reaction enables facile 1,2-aminoalkylation and 1,2-alkylarylation and exhibits a broad reaction scope and excellent functional group compatibility (>100 examples with up to 96% yield). It also provides a robust formal [2+2+1] cyclization strategy for the concise construction of pyrrolidine skeletons under mild reaction conditions. Mechanistic studies support an inner-sphere single electron transfer pathway for the successful cleavage of inert C-Br bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jianyang Dong, Fuyang Yue, Jianhua Liu, Hongjian Song, Yuxiu Liu, Qingmin Wang
Summary: The described Minisci reaction allows for the catalytic synthesis of heteroarylethyl alcohols by sequentially adding H2O and N-heteroarenes across olefinic double bonds. This scalable protocol enables direct hydroxy-heteroarylation of olefins with a wide range of N-heteroarenes and has the potential to rapidly convert abundant feedstock materials into medically relevant molecules.
Article
Chemistry, Multidisciplinary
Arun D. Kulthe, Prathama S. Mainkar, Srirama Murthy Akondi
Summary: A metal-free, three-component trifluoromethylative alkenylation reaction using beta-nitrostyrenes with unactivated alkenes has been developed under visible light, providing a series of trifluoromethylated aromatic alkenes in good to excellent yields.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Salman Khan, Akshay M. Nair, Chandra M. R. Volla
Summary: Herein, we report a mild metal-free visible-light-mediated allylation of thiols using an inexpensive photocatalyst (eosin Y). Photocatalytically generated sulfenyl radicals were coupled with allylic alcohols to obtain allylic sulfides in good to excellent yields. The reaction was found to be scalable and the products could be further functionalized. Furthermore, preliminary studies were carried out to gain insights into the reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Keishi Kohara, Aaron Trowbridge, Milo A. Smith, Matthew J. Gaunt
Summary: Visible-light-activated electron donor-acceptor complexes provide unique reaction pathways for the synthesis of complex molecules under mild conditions. This study demonstrates a method for the reductive generation of α-amino radicals through the reaction of a visible-light-activated ion-pair charge-transfer complex, allowing for the development of a multicomponent coupling reaction to form substituted aminomethyl-cyclopentanes. The operationally straightforward transformation is versatile and enables the generation of cyclic amine-containing scaffolds from readily available feedstocks.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Liubov Panferova, Alexander D. Dilman
Summary: This study describes the synthesis of pinacol boronic esters through the reaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron, followed by treatment with pinacol and triethylamine. The reaction is promoted by an organic photocatalyst (3DPA2FBN) under irradiation with 400 nm light, and is effective for primary, secondary, and tertiary sulfides. The electron depleting character of the fluorinated pyridine fragment is crucial in generating alkyl radicals.
Article
Chemistry, Organic
Jiaxin Liu, Yin Wei, Min Shi
Summary: A new method for the direct single-electron oxidation of methylenecyclopropanes (MCPs) was reported, leading to the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives through merging visible light photoredox catalysis and cobalt catalysis. In MeCN with Et3N·3HF, fluorinated derivatives were obtained in moderate yields, while in MeCN/HFIP, good yields were achieved through a MHAT process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yu Zhang, Jiahui Qian, Miao Wang, Yahao Huang, Peng Hu
Summary: An efficient and low-cost protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids catalyzed by iron salts under visible light is presented. This new method is highly efficient and scalable, and mechanistic studies have revealed the generation process of the key step.
Article
Chemistry, Organic
Fang Wei, Haoyu Li, Chuanling Song, Yudao Ma, Ling Zhou, Chen-Ho Tung, Zhenghu Xu
Article
Chemistry, Physical
Haoyu Li, Zengrui Cheng, Chen-Ho Tung, Zhenghu Xu
Article
Chemistry, Organic
Tingting Song, Haoyu Li, Fang Wei, Chen-Ho Tung, Zhenghu Xu
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Tingting Song, Lei Zhu, Haoyu Li, Chen-Ho Tung, Yu Lan, Zhenghu Xu
Article
Chemistry, Multidisciplinary
Haoyu Li, Xinxin Tang, Jia Hao Pang, Xiangyang Wu, Edwin K. L. Yeow, Jie Wu, Shunsuke Chiba
Summary: This study reveals the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. By photoexcitation of tetrasulfide dianions, single-electron reduction of aryl halides is achieved, leading to the participation of aryl radicals in cross-coupling, borylation, and hydrogenation reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Yuliang Liu, Haoyu Li, Shunsuke Chiba
Summary: A protocol for photoinduced cross-coupling of aryl iodides and alkenes has been developed, utilizing a radical cascade mechanism. This method enables selective coupling of iodides over other halogen leaving groups and is compatible with various functional groups on both arene and alkene motifs.
Editorial Material
Chemistry, Multidisciplinary
Haoyu Li, Shunsuke Chiba
Summary: This study presents a novel photocatalytic protocol for the radical borylation of reductively inert aryl electrophiles using simple thiolate salts as catalysts. The facile installation of functionalities to aromatic compounds via chemical activation of inert carbon-heteroatom bonds is demonstrated in this research.
Article
Chemistry, Multidisciplinary
Eugene Yew Kun Tan, Amirah S. Mat Lani, Wayne Sow, Yuliang Liu, Haoyu Li, Shunsuke Chiba
Summary: The facile construction of C(sp(3))-rich carbo- and heterocyclic compounds is an important synthetic strategy for contemporary drug discovery programs. In the presence of potassium formate and methanol under visible light irradiation, polysulfide anions can catalyze the dearomatization process of substituted naphthalenes, indoles, and other related heteroaromatic compounds. This method demonstrates broad functional group tolerance, operational simplicity, scalability, and cost-effectiveness, making it a practical and sustainable synthetic tool for arene dearomatization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Eugene Yew Kun Tan, Amirah S. Mat Lani, Wayne Sow, Yuliang Liu, Haoyu Li, Shunsuke Chiba
Summary: The study demonstrates a method using polysulfide anions to catalyze the dearomatization process under visible light irradiation. The developed protocol exhibits broad functional group tolerance, operational simplicity, scalability, and cost-effectiveness, making it a practical synthetic tool.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Haoyu Li, Shunsuke Chiba
Summary: A photocatalytic method using polysulfide anions as catalysts enables the synthesis of alpha-tertiary amines through alpha-C-H functionalization of a-secondary benzylamines with cyanoarenes or aryl ketones. The key factors include the highly negative oxidation potential of polysulfide dianions and the catenated structure of polysulfide anion radicals, facilitating the construction of sterically congested alpha-tertiary amine scaffolds.
Article
Chemistry, Physical
Yuliang Liu, Haoyu Li, Eugene Yew Kun Tan, Erik Budi Santiko, Youhei Chitose, Manabu Abe, Shunsuke Chiba
Summary: In this study, we demonstrated the design and synthesis of PIqs with electron-withdrawing groups, which exhibit wider redox windows and higher triplet-state energies under visible light irradiation. By modifying the positions and structures of these electron-withdrawing groups, the photophysical and electrochemical properties of PIqs can be tailored, enabling a range of molecular transformations driven by visible light.
Article
Chemistry, Multidisciplinary
Haoyu Li, Yuliang Liu, Shunsuke Chiba
Summary: This perspective summarizes recent advances in using sulfur anions to promote molecular transformations under visible light irradiation, with focus on the role of sulfur anions in different reaction modes.
Article
Chemistry, Multidisciplinary
Haoyu Li, Yuliang Liu, Shunsuke Chiba
Summary: A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been successfully developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Shuai Huang, Haoyu Li, Tian Xie, Fang Wei, Chen-Ho Tung, Zhenghu Xu
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.
