Article
Chemistry, Multidisciplinary
Wan-Lei Yu, Zi-Gang Ren, Wei Ma, Haixue Zheng, Wangsuo Wu, Peng-Fei Xu
Summary: In this study, an oxidant-free dehydrogenative amination of alkenes was achieved through synergistic photoredox and cobalt catalysis, resulting in the synthesis of a wide range of five-membered N-heterocycles with excellent atom-economy.
Article
Chemistry, Organic
Zheng-Hai Wang, Dong-Hui Wang
Summary: A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported, with moderate to good yields under mild reaction conditions. Large-scale syntheses of Ezutromid and Flunoxaprofe are demonstrated in one or two steps. The proposed catalytic mechanism involves Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation.
Article
Chemistry, Multidisciplinary
Hang Li, Na Li, Jinghao Wu, Tianyang Yu, Ran Zhang, Li-Ping Xu, Hao Wei
Summary: In this study, a method for direct insertion of an intramolecular nitrogen atom into an aromatic C-C bond was described. Carbamoyl azides were activated by a Rh catalyst and inserted directly into the C-C bond of an arene ring to produce fused azepine products. The use of a paddlewheel dirhodium complex effectively inhibited the undesired C-H insertion. Density functional theory calculations were used to elucidate the reaction mechanism and chemoselectivity of the Rh-catalyzed reactions. The resulting fused azepine products are highly stable and can be further diversified.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Matteo Corrieri, Lucia De Crescentini, Fabio Mantellini, Giacomo Mari, Stefania Santeusanio, Gianfranco Favi
Summary: A practical and environmentally friendly approach for the synthesis of pyrrolo[2,3-b]indoles has been developed using an intramolecular C-H bond amination reaction. This chemoselective transformation, which operates at 50 degrees C in water without the need for base or oxidant, relies on a Cu/Fe co-catalyst system. The easy product isolation and recyclability of the catalyst make it a promising method for the synthesis of fused N-heterocycles in pharmaceutical and medicinal chemistry.
Article
Chemistry, Multidisciplinary
Chang Wang, Xiaodong Fan, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A rhodium-catalyzed annulation of vinylene carbonate with amidines was developed in this paper, leading to 4-methylquinazolines with moderate to excellent yields. The procedure proceeded by sequential ortho-acylation and annulation, utilizing vinylene carbonate as the acetylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Xin Nie, Zihan Yan, Sergei Ivlev, Eric Meggers
Summary: Enantioselective C(sp(3))-H aminations provide an efficient access to nonracemic chiral amines. This work describes the catalytic asymmetric synthesis of chiral 1,2,5-thiadiazolidine-1,1-dioxides using a recently introduced simple chiral ruthenium bis(oxazoline) complex, achieving high yields and enantioselectivities. Mechanistic experiments confirmed a stepwise mechanism and demonstrated that the cyclic sulfamide products are suitable for the synthesis of chiral vicinal diamines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Dayou Zhong, Lin-Yang Wu, Xing-Zhen Wang, Wen-Bo Liu
Summary: A redox-neutral Fe-catalyzed intramolecular C-H amidation of N-benzoyloxyureas was developed, utilizing a simple iron complex generated in situ from Fe(OTf)(2) and bipyridine as the catalyst, and N-benzoyloxyureas as the nitrene precursors without the need for external oxidants. The methodology allowed for the synthesis of a variety of cyclic ureas via aliphatic C(sp(3))-H amidation with excellent yields, and was also applicable to aryl C(sp(2))-H nitrene insertion to provide benzimidazolones in moderate yields.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Editorial Material
Chemistry, Multidisciplinary
Dipankar Sahoo, Diana A. Iovan
Summary: A recent study reported the isolation and characterization of an N-trifluoromethyl-substituted Fe(IV) bisimido species that undergoes intramolecular C-H activation. This discovery opens up new possibilities for N-group-transfer chemistry.
Article
Chemistry, Organic
Tzu-Lun Liu, Meng-Li Jhou, Cheng-En Hsieh, Chia-Jung Lin, Hsiu-Hui Su, Chih-Ming Chou
Summary: This study presents a protocol for the preparation of functionalized N-allyl-N-aryl sulfonamides via palladium-catalyzed intramolecular decarboxylative N-allylation reaction, showing good regioselectivity. Additionally, transformation of N-allyl-N-aryl sulfonamide into 4-aryl-1,2,3,4-tetrahydroquinoline and nitrogen-containing beta-hydroxysulfide bioactives has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Jiao Ma, Liuli Dong, Jiarong Yao, Aijun Lin, Hequan Yao
Summary: This article describes a selenium-catalyzed intramolecular oxidative amination of cyclopentenes, which allows the synthesis of various 2-azabicyclo[2.2.1]heptenes with yields ranging from 58% to 96%. The reaction conditions are mild, and the substrate scope is broad. The subsequent modification of the bicyclic backbone and amino group further demonstrates the application value of this aza-bridged ring.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Ruo-Xing Jin, Jing-Cheng Dai, Yan Li, Xi-Sheng Wang
Summary: This article describes a copper-catalyzed intramolecular amination via the cross-coupling of C(sp(3))-H and N-H bonds of secondary amine. The method exhibits excellent chemo- and regioselectivity, extensive substrate scope, and good to excellent tolerance towards various functional groups, offering an efficient pathway to construct nitrogen-containing heterocycle skeletons.
Article
Chemistry, Organic
Hongwu Jiang, Kaiwen Li, Shuangfeng Dong, Zhuqi Chen, Guochuan Yin
Summary: In this study, a Pd(II)/LA-catalyzed oxidative C-H amination reaction of 2-acetaminobiphenyls was reported, using dioxygen balloon as the sole oxidant source to construct carbazoles. The presence of LA greatly improved the catalytic efficiency of Pd(OAc)(2). Remarkably, in certain cases, the annulation product underwent deacetylation under standard conditions to afford free carbazoles as the final product. H/D exchange studies confirmed the reversibility of C-H activation and revealed multiple C-H activation sites using -NAc and -NTs as directing groups. Additionally, the palladacycle compound was identified through H-1 NMR characterizations and proved to be the intermediate prior to carbazole formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Young Ho Kim, Dong Bin Kim, Su San Jang, So Won Youn
Summary: A Pd-catalyzed intramolecular allylic C-H amination method has been developed, allowing for the synthesis of diverse 1,3-X,N-heterocycles through selective allylic C-H cleavage and pi-allylpalladium formation. The use of substrates containing a labile allylic moiety and new catalytic systems overcomes significant challenges for achieving highly chemo- and regioselective allylic C-H amination.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Arne G. A. Geissler, Jasmin R. Riesterer, Bernhard Breit
Summary: The intramolecular addition of tosylureas to allenes is highly diastereoselective with palladium or rhodium catalysis, yielding 1,3-cyclic ureas. Palladium catalysis allows access to thermodynamic anti-tetrahydropyrimidinones, while rhodium catalysis enables synthesis of kinetic syn-tetrahydropyrimidinones, both with excellent yields and diastereoselectivities. The obtained tetrahydropyrimidinones are easily deprotected and modified, demonstrating their synthetic value.
Article
Chemistry, Multidisciplinary
Wowa Stroek, Martin Keilwerth, Daniel M. Pividori, Karsten Meyer, Martin Albrecht
Summary: The synthesis of N-heterocycles is crucial for the pharmaceutical industry, and a greener alternative using direct intramolecular C-H amination has been explored. A new iron-based complex catalyst was developed in this study, which can catalyze reactions without the need for protecting groups and achieved a significantly higher turnover number compared to other reported systems.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Joydip De, Rohit Ashok Kumar Yadav, Rahul Singh Yadav, Santosh Prasad Gupta, Mayank Joshi, Angshuman Roy Choudhury, Jayachandran Jayakumar, Jwo-Huei Jou, Chien-Hong Cheng, Santanu Kumar Pal
Summary: A unique strategy involving a central benzene core with specific attachments led to the attainment of discotic nematic phase in the reported compounds. These compounds exhibit high solid-state emission and act as efficient deep-blue emitters in OLEDs with CIEx,y coordinates of (0.16, 0.07).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Krishan Kumar, Kiran Kishore Kesavan, Diksha Thakur, Subrata Banik, Jayachandran Jayakumar, Chien-Hong Cheng, Jwo-Huei Jou, Subrata Ghosh
Summary: The performance of newly developed functional pyrene derivatives with different functionalized pyridine units as hole-transporting materials for OLED applications was studied, showing stable performance and desirable characteristics in terms of electro-optical properties and device performance.
Article
Chemistry, Multidisciplinary
Yi-Kuan Chen, Jayachandran Jayakumar, Chia-Min Hsieh, Tien-Lin Wu, Chun-Cheng Liao, Jayabalan Pandidurai, Chang-Lun Ko, Wen-Yi Hung, Chien-Hong Cheng
Summary: The TPAmPPC compound is a highly efficient TADF material with excellent optical properties, demonstrating high photoluminescence quantum yields and superior device performance in OLEDs.
ADVANCED MATERIALS
(2021)
Review
Chemistry, Organic
Lusina Mantry, Rajaram Maayuri, Vikash Kumar, Parthasarathy Gandeepan
Summary: C-H functionalization has emerged as a powerful strategy in organic synthesis, offering improved economy and unique reaction pathways compared to traditional methods. Nickel catalysts in photoredox C-H functionalization have garnered significant attention for their relative earth-abundance and cost-effectiveness.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Vijaykumar H. Thorat, Yu-Lin Tsai, Yong-Ran Huang, Chien-Hong Cheng, Jen-Chieh Hsieh
Summary: In this study, a nickel-catalyzed cyclization reaction was reported, which allowed the generation of polysubstituted biaryl sultams by reacting 1,2,3,4-benzothiatriazine-1,1-dioxides with arynes. The reaction exhibited high tolerance towards substituents on every subunit. Mechanistic investigation revealed the formation of a diradical intermediate, which reacted with a nickel complex to form a nickelacycle intermediate and underwent subsequent cyclization through aryne insertion.
Review
Chemistry, Organic
Rajaram Maayuri, Parthasarathy Gandeepan
Summary: Transition metal-catalyzed C-H activation has shown promise in organic synthesis, with manganese catalysts exhibiting unique and promising reactivity, particularly in the hydroarylation of multiple bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Vikash Kumar, Rajaram Maayuri, Lusina Mantry, Parthasarathy Gandeepan
Summary: Rhodium-catalyzed C-H activation is a powerful tool for synthesizing C-C and C-heteroatom bonds. However, the use of stoichiometric chemical oxidants limits the sustainability of these transformations. The emergence of metalla-electrocatalysis, which combines transition metal catalysis and electrochemistry, offers a sustainable and efficient approach for constructing organic molecules. This review summarizes the recent developments, challenges, and opportunities in rhodium-catalyzed electrochemical C-H activation transformations.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Upasana Deori, Ezhakudiyan Ravindran, Gyana Prakash Nanda, Suman G. Ramanath, Upasha Acharya, Parthasarathy Gandeepan, Pachaiyappan Rajamalli
Summary: This study designed and synthesized two anthracene based compounds, which exhibit multifunctional properties including aggregation-induced emission (AIE), multi-responsive polymorphs, mechanoluminescence, and electroluminescence. By controlling the temperature, three polymorphic phases were achieved from one of the compounds, showing different emission colors under mechanical stimuli. Additionally, the compounds were used as emitters in blue and green organic light-emitting diodes (OLEDs), achieving high external quantum efficiency.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Nanoscience & Nanotechnology
Sheng-Lin Deng, Yi-Kuan Chen, Jian Lei, Jayachandran Jayakumar, Chang-Lun Ko, Wen-Yi Hung, Tien-Lin Wu, Chien-Hong Cheng
Summary: The acceptor modification strategy is an effective method for tuning the emission color of TADF emitters. In this study, three TADF emitters with donor-acceptor structures were successfully synthesized, demonstrating greenish-yellow to orange-red emissions with high photoluminescent quantum yields in thin films. The nondoped OLEDs based on TPAmbPPC exhibited a remarkable EQE(max) of 21.6%, indicating its promising potential for OLED applications. Orange-red OLED devices based on TPAmCPPC showed high EQE(max), CE, and PE values.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Vikash Kumar, Rajaram Maayuri, Kapil Medhi, Parthasarathy Gandeepan
Summary: Here, we report a rhodium(III)-catalyzed C-H/N-H activation and annulation approach for obtaining pyrimidoindolones from N-carbamoylindoles and vinylene carbonate. The reaction occurs at room temperature and does not require any external oxidants. A diverse spectrum of indoles were demonstrated to be viable substrates capable of producing the desired pyrimidoindolones in high yields. In addition, the reaction scope has been expanded to include pyrrole substrate. Furthermore, detailed mechanistic studies have been performed to delineate the working mode of the reaction.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Vikash Kumar, Parthasarathy Gandeepan
Summary: A mild and convenient method for synthesizing 3,4-unsubstituted isoquinolones from N-methoxybenzamides and vinylene carbonate has been achieved using a versatile rhodium(III) catalyst. The reaction proceeds at room temperature in biomass derived ethanol solvent and avoids the use of stoichiometric external oxidant. The mechanistic studies suggest facile and reversible chelation-assisted C-H rhodation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Chia-Min Hsieh, Yi-Kuan Chen, Jian Lei, Pang-Yu Chou, Song-Ting Hsieh, Chang-Lun Ko, Wen-Yi Hung, Tien-Lin Wu, Chien-Hong Cheng
Summary: In this study, a diboron-based molecule, PhCzDBA, is designed and its OLED device exhibits high EQE and stability, with low efficiency roll-off and long operational lifetimes. It shows potential and diverse applications in future display technology.
ACS MATERIALS LETTERS
(2023)
Article
Materials Science, Multidisciplinary
Yi-Kuan Chen, Jayachandran Jayakumar, Chang-Lun Ko, Wen-Yi Hung, Tien-Lin Wu, Chien-Hong Cheng
Summary: Three pyridine-carbonitrile (PPC) fluorophores with amine-type donors were designed and synthesized, showing high photoluminescence quantum yields, thermally activated delayed fluorescence (TADF) and thermal stability. By modifying the donors, the horizontal dipole orientation ratios were successfully increased. One of the dopants exhibited high external quantum efficiency and low driving voltage in a green OLED.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Materials Science, Multidisciplinary
Jayabalan Pandidurai, Jayachandran Jayakumar, Yi-Kuan Chen, Chia-Min Hsieh, Chien-Hong Cheng
Summary: This study focuses on the design, synthesis, and investigation of four new TADF emitters, aiming to achieve high internal quantum efficiency and external quantum efficiency through optimizing molecular structures and controlling intermolecular interactions. The results show that the Y-shaped emitters exhibit high photoluminescence quantum yields and efficient TADF, with important roles played by intramolecular interactions and hydrogen bonds in enhancing molecular rigidity and improving efficiency.
JOURNAL OF MATERIALS CHEMISTRY C
(2021)
Article
Materials Science, Multidisciplinary
Bahadur Sk, Vasudevan Thangaraji, Nisha Yadav, Gyana Prakash Nanda, Sannibha Das, Parthasarathy Gandeepan, Eli Zysman-Colman, Pachaiyappan Rajamalli
Summary: In this study, non-doped delayed fluorescence organic light-emitting diodes (OLEDs) were successfully achieved through the design and synthesis of two new organic light-emitting materials. These devices exhibit high luminance, efficiency, and minimal efficiency roll-off, showcasing the potential for high performance in device fabrication.
JOURNAL OF MATERIALS CHEMISTRY C
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
