Review
Chemistry, Multidisciplinary
Sheng Zhang, Xiujuan Feng, Ming Bao
Summary: Transition-metal catalyzed multi-component reactions have attracted attention in organic and drug synthesis due to their simplicity, availability of raw materials, and lack of intermediate separation. Among these reactions, three-component processes have become effective organic procedures. This article reviews the development of benzylpalladium intermediates in the rapid construction of two new chemical bonds.
Review
Chemistry, Inorganic & Nuclear
Pengcheng Gao, Michal Szostak
Summary: The catalytic addition of water to unsaturated C-C or C-N p bonds is an important and environmentally sustainable method for forming C-O bonds. Traditional acid-catalyzed hydration requires strong acids or toxic mercury salts, limiting its practical applications and posing safety and environmental concerns. Transition-metal-catalyzed hydration with NHC ligands has gained significant attention and has achieved major progress. This review provides a comprehensive overview of hydration reactions catalyzed by transition metal-NHC complexes and their applications in catalytic hydration.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Organic
Raphael K. Klake, Joshua D. Sieber
Summary: In this study, a Cu-catalyzed aminoallylation of aldehyde electrophiles through reductive coupling was developed by avoiding the competitive reduction of the aldehyde electrophile by a CuH catalyst. This process resulted in a highly diastereo- and enantioselective synthesis of chiral 1,2-aminoalcohols with secondary alcohol substitution. Cleavage of the N substituents on the reaction products allowed access to the other diastereomer of the aminoalcohol, which was studied in the context of a synthesis of eligulstat.
Article
Chemistry, Multidisciplinary
Qiqige Qiqige, Rylan J. Lundgren, Duanyang Kong
Summary: Stereodivergent dual catalysis is a powerful tool for selectively preparing four stereoisomers from molecules with two chiral centers. However, generating molecules with three newly formed stereocenters using dual catalyst approaches remains challenging.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Stephen Collins, Joshua D. Sieber
Summary: In this study, we present an improved system for the Cu-catalyzed enantioselective reductive coupling of ketones and allenamides by optimizing the allenamide to prevent on-cycle rearrangement. High enantioselectivities were achieved for various ketones. Unlike cyclic allenamides, which favor the syn-form, the acyclic allenamides described in this work selectively generated anti-diastereomers. A rationalization for this change in diastereoselectivity is also provided.
Review
Chemistry, Applied
Chenfei Guan, Huijie Qi, Linjun Han, Guofu Zhang, Chengrong Ding
Summary: Aryl fluorosulfates (ArOSO2F/ArOFs) are versatile synthons widely used in click chemistry for their extensive applications in fields such as biology, medicine, materials, and polymers. They can be readily prepared from phenolic compounds found in nature and are considered an economical, efficient, and environmentally friendly alternative to trifluoromethane sulfonates. Recently, the use of fluorosulfates as electrophilic reagents in transition-metal-catalyzed coupling reactions has gained attention, and the development of a wide range of coupling reactions will greatly expand their applications in interdisciplinary fields.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Raphael K. Klake, Mytia D. Edwards, Joshua D. Sieber
Summary: A new catalytic enantioselective addition method utilizing copper-catalyzed reductive coupling to add N-substituted allyl equivalents to ketones has been developed, accessing important chiral 1,2-aminoalcohol synthons with high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed, including the identification of a reversible ketone allylation step previously unreported in copper-catalyzed reductive coupling.
Article
Chemistry, Organic
Yulei Zhu, Yaxin Zeng, Zhong-Tao Jiang, Ying Xia
Summary: Gem-difluorinated cyclopropanes, as a special class of compounds, have attracted much attention due to their unique properties. Recently, they have emerged as a novel synthons for the synthesis of monofluoroalkenes through cross-coupling reactions.
Review
Chemistry, Multidisciplinary
Subhabrata Dutta, Trisha Bhattacharya, Daniel B. Werz, Debabrata Maiti
Summary: Allylation reactions, pioneered by Tsuji and Trost, are essential C-C bond-forming transformations with broad applications in synthetic chemistry, bioactive compounds, and pharmaceutical industries. The development of synthetic strategies and the emergence of site-selective C-H activation have further expanded the scope of allylation reactions, eliminating the need for pre-functionalized substrates and activated allylating reagents.
Article
Chemistry, Organic
Jie Huang, Ling-Ling Chen, Zhi-Min Chen
Summary: A palladium-catalyzed regioselective 1,2-alkynyl-carbonalization of conjugated dienes with ethynylbenziodazolone (EBZ) and indoles has been developed, providing easy access to various molecules containing alkenyl, alkynyl, and indole groups. The resulting products are also suitable for various derivatizations.
Article
Chemistry, Physical
Chaoyan Ma, Can Li, Jiahui Bai, Junzhe Xiao, Yizhan Zhai, Yinlong Guo, Shengming Ma
Summary: In this study, a rhodium-catalyzed C-H functionalization-based intermolecular allylation of indoles with trisubstituted allenes has been developed. The synthetic process demonstrates excellent regioselectivity, Z-selectivity, high efficiency of chirality transfer, and a wide tolerance of reactive functional groups under mild conditions. Late-stage modification on complex bioactive or drug molecules has been achieved, along with various synthetic transformations. A reaction mechanism has been proposed based on mechanistic experiments and SAESI-MS studies.
Article
Chemistry, Physical
Yulong Song, Chunling Fu, Shengming Ma
Summary: A copper-catalyzed three-component reaction has been developed for the synthesis of 1,7-double-functionalized allenes, which are difficult to prepare. The allenyl nitrile products demonstrate their potential as platform molecules in synthesis.
Article
Chemistry, Organic
Dang Binh Ho, Samantha Gargaro, Raphael K. Klake, Joshua D. Sieber
Summary: In this work, a modified catalytic system utilizing a commercially available Cu-phosphite catalyst is developed for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral gamma-lactone precursors with asymmetric ratios ranging from 80:20 to 99:1.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jichao Xiao, Zhenning Li, John Montgomery
Summary: This study demonstrates a method using nickel catalysis and BiOx ligand for the reductive coupling of redox-active esters with aliphatic aldehydes to obtain silyl-protected secondary alcohols. The protocol is simple, mild, and tolerates a variety of functional groups, with potential mechanistic insights pointing towards a radical chain pathway.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Junjie Fan, Xiaoyan Wu, Chunling Fu, Shengming Ma
Summary: Here we report a Cp*RhCl2-catalyzed three-component coupling cyclization of 2,3-allenoic acids and 2,3-allenols in the presence of Cu(OAc)(2)center dot H2O, resulting in the formation of furanone derivatives. The synthetic potential of this reaction has been demonstrated, and isotopic labeling experiments have revealed unexpected reaction pathways.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Nanoscience & Nanotechnology
Vasudevan Thangaraji, Pachaiyappan Rajamalli, Jayachandran Jayakumar, Min-Jie Huang, Yu-Wei Chen, Chien-Hong Cheng
ACS APPLIED MATERIALS & INTERFACES
(2019)
Article
Chemistry, Multidisciplinary
Ya-Chun Hong, Rajagopal Santhoshkumar, Chien-Hong Cheng
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Lin-Chieh Cheng, Wei-Chen Chen, Rajagopal Santhoshkumar, Tzu-Hsuan Chao, Mu-Jeng Cheng, Chien-Hong Cheng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
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
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
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
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
Indu Bala, Rohit Ashok Kumar Yadav, Manisha Devi, Joydip De, Nitya Singh, Kamalakannan Kailasam, Jayachandran Jayakumar, Jwo-Huei Jou, Chien-Hong Cheng, Santanu Kumar Pal
JOURNAL OF MATERIALS CHEMISTRY C
(2020)
Article
Materials Science, Multidisciplinary
Jayabalan Pandidurai, Jayachandran Jayakumar, Natarajan Senthilkumar, Chien-Hong Cheng
JOURNAL OF MATERIALS CHEMISTRY C
(2019)
Article
Chemistry, Organic
Yu-Che Chang, Sekar Prakash, Chien-Hong Cheng
ORGANIC CHEMISTRY FRONTIERS
(2019)
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)