Article
Chemistry, Organic
Xandro Vidal, Jose Luis Mascarenas, Moises Gulias
Summary: The palladium-catalyzed formal (4 + 2) cycloaddition reaction described in the study offers a direct and unconventional approach to tetrahydroquinoline skeletons through the activation of C(sp(3))-H bonds. The reactivity can also be extended to ortho-methyl benzylamides, allowing for the assembly of appealing tetrahydro-2-benzazepines in a formal (5 + 2) annulation process.
Article
Chemistry, Applied
Hayeon Kwak, Eunsu Kang, Jae Yeong Song, Geunhee Kang, Jung Min Joo
Summary: The development of modular approaches for heteroaromatic cores and substituents is crucial for drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The Pd catalytic system transformed a variety of five-membered heteroarenes to the corresponding benzofused products, demonstrating its versatility in the annulation of (hetero)aromatic rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yuan He, Jing Zheng, Lin Dong
Summary: A new rhodium(iii)-catalyzed multistep cascade spirocyclization approach using oxadiazoles as the directing group was developed to synthesize a novel N-acetyl chain of spiropyrroloisoquinoline derivatives. This one-pot reaction also isolates aryloxadiazole derivatives as cross-coupling intermediates, effectively expanding the scope of isoquinoline and aryloxadiazole skeletons.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Weidan Yan, Hong Luo, Qiling Wu, Liansheng Liu, Jing Li, Junfa Wei
Summary: A Cp*RhIII-catalyzed efficient synthesis of isoquinolin-3-ol derivatives bearing a pyridinyl ring using imidate as a directing group under C-H activation strategy with pyridotriazoles as carbene reagents is reported. In this reaction, cascade C-H activation, regioselective cyclization, and elimination occur in one pot. The present methodology featured a good range of functional group tolerance and furnished the target products in moderate-to-excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ramesh Kotipalli, Undamatla Suri Babu, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: Here, we report a novel selective annulation reaction using a Rh-catalyst, which allows the synthesis of pyranoindole cyclic motifs by reacting indolyl oxopropanenitrile with hydroxy-alkynoates. The reaction takes advantage of the unique reactivity of enol oxygen, resulting in regio- and stereoselective assembly of the desired compounds through a five-membered oxy-rodacycle formed via C-H activation guided by enolic- and propargyloxy dual coordination.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jia-Yin Wang, Sai Zhang, Yao Tang, Shenghu Yan, Guigen Li
Summary: The Cu(I)-catalyzed annulation-halotrifluoromethylation and cyanotrifluoromethylation of enynones have been successfully developed, allowing for the construction of quaternary carbon-centered 1-indanones through multibond formations with moderate to good chemical yields. The reaction of enynones with Togni's reagent and chloro- or bromotrimethylsilane yielded halo- and CF3-containing 1-indenones, while the addition of K3PO4 as a base resulted in the formation of cyano-anchored (Z)-1-indanones as the major stereoisomeric products. This strategy exhibits excellent compatibility with a wide range of enynones.
Article
Chemistry, Organic
De-Yong Yang, Liang Liu, Jia-Yi Gu, Yan-Hong He, Zhi Guan
Summary: A visible-light-initiated radical cascade reaction was developed for the synthesis of structurally diverse fused Indolo-pyridones. This telescoped method bypasses the need for lengthy prefunctionalization steps of radical precursors, allowing rapid construction of valuable architectures with superior compatibility with C-centered radicals.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuan He, Xian-Zhang Liao, Lin Dong, Fen-Er Chen
Summary: The study presents a novel synthetic method for efficiently constructing N-oxopropyl chains of isoquinolone derivatives, which has high research and application value.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Attunuri Nagireddy, Dattatri, Ramesh Kotipalli, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: This research presents a rhodium-catalyzed oxidative three-point double annulation of enaminones with propargylic alcohols to access arylnaphthalene-based lignan derivatives. The key step involves the regioselective insertion of propargylic alcohol into the rhoda-cycle due to hydroxyl rhodium coordination, with mechanism determined through control experiments and KIE studies.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chunyang Liu, Xiaoyan Shangguan, Yan Li, Qian Zhang
Summary: A novel radical cascade strategy was developed for the synthesis of highly functionalized cyclobutenes directly from cyclobutanes. This method involves rare cleavage of four or five C-H bonds and formation of two C-N/C-S or three C-Br bonds.
Article
Chemistry, Physical
Tyler G. Saint-Denis, Nelson Y. S. Lam, Nikita Chekshin, Paul F. Richardson, Jason S. Chen, Jeff Elleraas, Kevin D. Hesp, Daniel C. Schmitt, Yajing Lian, Chan Woo Huh, Jin-Quan Yu
Summary: Enantioselective C(sp(3))-H activation has attracted significant interest, but the mechanisms responsible for enantioselection remain unclear. This study found extreme sensitivity differences in two substrate classes, leading to high enantiomeric ratios for thioether-directed-C(sp(3))-H arylation. The exploitation of transient chirality at sulfur was key to achieving stereochemical information transfer from ligand backbone to substrate carbons.
Article
Chemistry, Multidisciplinary
Yong Zhang, Ya-Kui Sun, Ya-Ping Chang, Hui Shao, Yu-Ming Zhao
Summary: The rapid construction of molecules with all-substituted quaternary stereocenters is a significant but challenging task in organic synthesis. This study reports a novel palladium-catalyzed cascade reaction between alkene-tethered aryl iodides and carbon monoxide, providing a practical and powerful method for synthesizing complex polycyclic molecules containing aryl-substituted quaternary stereocenters. Mechanistic studies suggest that the reaction proceeds through a Heck-type carbonylative cyclization followed by a ketene-involved Friedel-Crafts acylation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Shaofeng Li, Hanyu Nie, Mengyan Duan, Wenfei Wang, Congjun Zhu, Chuanjun Song
Summary: This work presents a strategy for the one-pot synthesis of protoberberine alkaloid derivatives using palladium catalyzed cascade alpha-arylation and cyclization, resulting in moderate to excellent isolated yields. The protocol provides an efficient and convenient path to multisubstituted protoberberine derivatives and can directly yield natural alkaloids.
Article
Chemistry, Organic
Xing Chen, Mengke Li, Zhipeng Liu, Can Yang, Haisheng Xie, Xinwei Hu, Shi-Jian Su, Huanfeng Jiang, Wei Zeng
Summary: An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle, resulting in silaarenes with aggregation-induced emission behavior. Mechanistic investigations revealed that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.
Article
Chemistry, Multidisciplinary
Muniganti Naveen Kumar, Vavilapalli Suresh, Attunuri Nagireddy, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: Annulations of unsaturated systems through C-H activation are a powerful tool for producing multicyclic scaffolds. Employing a dual coordination strategy with coordinating centers in both annulation partners can lead to remarkable selectivities. In this study, we report a Pd-catalyzed regioselective rollover cascade dual C-H annulation for constructing phenanthrene scaffolds. Mechanism studies, including control experiments, KIE, and deuteration experiments, were conducted, and downstream transformations and scaled-up reactions were performed to evaluate the robustness of the transformation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Subramani Kumaran, Rajendhiran Saritha, Palanivelu Gurumurthy, Kanniyappan Parthasarathy
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Sampath Thavaselvan, Kanniyappan Parthasarathy
Article
Chemistry, Organic
Vijaykumar H. Thorat, Jen-Chieh Hsieh, Chien-Hong Cheng
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)
Article
Chemistry, Organic
Subramani Kumaran, Kanniyappan Parthasarathy
Summary: An efficient Rh(III)-catalyzed cross-dehydrogenative coupling of N-pyridinylindoles with benzo[b]thiophene 1,1-dioxides has been developed via directing-group-assisted C-H activation, forming a new C-C bond from two inert C-H bonds in a one-pot reaction. The synthesized compounds exhibit compatibility with various functional groups and their emission properties have been explored.
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.
Article
Chemistry, Organic
Subramani Kumaran, Kanniyappan Parthasarathy
Summary: A new and efficient protocol for the synthesis of benzothiadiazinoisoquinoline 6,6-dioxides and benzothiadiazinoisoindole 5,5-dioxides has been demonstrated. These compounds are formed through a sequential Rh(III)-catalyzed C-H cyclization of dihydrophenylbenzothiadiazine 1,1-dioxides with alkynes and oxidative Heck coupling/aza-Michael addition of dihydrophenylbenzothiadiazine 1,1-dioxides with acrylates, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Palanivelu Gurumurthy, Sampath Thavaselvan, Rajini Raja, Kanniyappan Parthasarathy
Summary: We developed an efficient method for the synthesis of 5,6-diarylnaphthoimidazo[2,1-b]thiazoles from 6-arylimidazo[2,1-b]thiazoles with alkynes through rollover C-H activation strategy using Rh(III)-catalyst. Alternatively, imidazo[2,1-b]thiazole fused isoquinolinium tetrafluoroborate salts have also been obtained with good yields by tuning the reaction conditions.
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
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
Chemistry, Organic
Sampath Thavaselvan, Kanniyappan Parthasarathy
Summary: This study describes a Ni(ii)-catalyzed aromatic homologation reaction of various directing groups with alkynes, leading to highly substituted naphthalene products through C-X bond cleavage, alkyne insertion, and C-H activation, with moderate to good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(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)
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)
