Article
Chemistry, Physical
Jiangjie Zhang, Jun Ying, Xiao-Feng Wu
Summary: A novel palladium-catalyzed tandem cyclization and carbonylation reaction was developed for the synthesis of indeno[1,2-b]indol-10(5H)-one derivatives. The reaction proceeded smoothly with high yields using formic acid as the CO source. This method can also be applied for the modification of various bioactive molecules.
JOURNAL OF CATALYSIS
(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
Chemistry, Physical
Hui-Qing Geng, Wei Wang, Xiao-Feng Wu
Summary: A nickel-catalyzed carbonylative synthesis of dihydrobenzofurans has been developed, using Mo(CO)(6) as the CO source and manganese metal as the reductant, to react alkyl halides with aryl iodides to give the desired products in moderate to good yields.
CATALYSIS COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Siqi Wang, Jian-Shu Wang, Zhengjie Le, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed dicarbonylation reaction has been developed for the synthesis of aryl esters from p-benzoquinones and aryl triflates using Cr(CO)(6) as the CO source. The reaction proceeds smoothly and efficiently, yielding a series of aryl esters in moderate to good yields (up to 90%).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Aleksandra Blocka, Jakub Ostapko, Wojciech Chaladaj
Summary: For the first time, a cascade reaction involving a 5-exo-dig intramolecular nucleophilic addition of an enamine to a terminal alkyne followed by cross coupling has been demonstrated. This reaction allows for the stereoselective formation of two new C-C bonds using a single Pd-complex capable of catalyzing two mechanistically diverse transformations. Mechanistic investigations revealed that cyclization, relying on the facile displacement of OTf weakly bound to the Pd-center by the alkyne, is the rate limiting step.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Shangyuan Wang, Jiajun Zhao, Jun Ying, Xiao-Feng Wu
Summary: This study developed a palladium-catalyzed one-pot two-step radical mediated carbonylative cyclization method to construct polycyclic 3,4-dihydroquinolin-2-(1H)-one scaffolds using perfluoroalkyl iodides and Mo-(CO)(6) with 1,7-enynes. Various polycyclic 3,4-dihydroquinolin-2-(1H)-one derivatives containing perfluoroalkyl and carbonyl units were synthesized with high yields. Moreover, modification of several bioactive molecules was demonstrated using this protocol.
Article
Chemistry, Organic
Xue-Song Li, Dan-Tong Xu, Zhi-Jie Niu, Ming Li, Wei-Yu Shi, Cui-Tian Wang, Wan-Xu Wei, Yong-Min Liang
Summary: The tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols catalyzed by gold provides a atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction involves 5-endo-dig cyclization/Meyer-Schuster rearrangement/Friedel-Crafts-type pathway, forming three C-C bonds and one C-O bond to give a polycyclic skeleton in a one-pot process. Additionally, the products exhibit unique optical properties, indicating their potential application value.
Article
Chemistry, Organic
Abdullajon Odilov, Hongjian Qin, Emmanuel Mintah Bonku, Fuqiang Zhu, Feipu Yang, Jingshan Shen
Summary: This paper presents a new method for the synthesis of an intermediate of telmisartan, where the Pd-catalyzed carbonylative cyclization reaction efficiently yields the target product while avoiding the use of other harmful chemicals.
Article
Chemistry, Physical
Dan Wen, Xing Ge, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes has been developed. A wide range of carboxamide substituted 2-pynones were obtained in moderate to high yields with quite high functional group compatibility using nitroarenes as the nitrogen sources and Mo(CO)6 as both CO surrogate and reductant. Late-stage modifications of natural molecules were also achieved.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Dmitrii Kalinin, Trond Ulven
Summary: A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)-aryl ketones is described. The protocol utilizes the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure to facilitate the carbonylative coupling between various C-(sp3)-hybridized organozinc reagents and a wide range of aryl iodides, including substrates with aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shangyuan Wang, Jiangjie Zhang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed cascade radical cyclization and carbonylation reaction of 1,7-enynes with perfluoroalkyl iodides and alcohols has been developed. The use of benzene-1,3,5-triyl triformate (TFBen) as the CO source enables the construction of 3,4-dihydroquinolin-2(1H)-one skeletons with the incorporation of both perfluoroalkyl and carbonyl units. This method provides a facile and efficient approach for the synthesis of various 3,4-dihydroquinolin-2(1H)-one derivatives with moderate to high yields and excellent E/Z selectivity.
Article
Chemistry, Organic
Ting-Ting Deng, Jie Huang, Guo Lian, Wen-Wu Sun, Bin Wu
Summary: A convenient and efficient synthetic protocol for the preparation of pyrimidoquinazolinone was established through Pd(II)-catalyzed carbonylative cyclization of N-aryl-2-aminopyrimidines with Mo(CO)(6) as carbon monoxide source. A series of 6H-pyrimido[2,1-b]quinazolin-6-one derivatives were obtained in good yields, and scale-up synthesis was investigated in this study.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Raffaella Mancuso, Alex De Salvo, Patrizio Russo, Aurelia Falcicchio, Nicola Della Ca, Leonardo Pantoja Munoz, Bartolo Gabriele
Summary: The PdI2/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols selectively produces dihydrofuroquinolinone derivatives in fair to high yields (60%-89%) and excellent turnover numbers (180-267 mol of product per mol of Pd) over 19 examples. This reaction involves the catalytic construction of two rings and three new bonds in one step, providing high value added fused heterocyclic structures from readily available materials.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Siyuan Wang, Yangkun Zhou, Hanmin Huang
Summary: A palladium-catalyzed tandem reaction has been developed to synthesize bridged polycyclic compounds. This method efficiently transforms a variety of alkenes and aldehyde-tethered benzylhalides into the desired products, providing a unique approach to complex lactone-containing bridged polycyclic compounds.
Article
Chemistry, Organic
Zhuang-Zhuang Li, Wan-Di Li, Juan Fan, Jun-Ting Li, Zhong-Wen Liu, Xian-Ying Shi
Summary: Silver trifluoroacetate with dual functions is demonstrated as a convenient in situ CO source and oxidant in the palladium-catalyzed oxidative carbonylative [4 + 1] annulation of aromatic acids to construct phthalic anhydride. Mechanistic studies reveal the sequential reactions of carboxyl-assisted C-H bond activation, insertion of the in situ released CO from silver trifluoroacetate, and reductive elimination. This protocol offers simple reaction conditions and operation without the need for gaseous CO, additives, ligands, or additional CO sources or oxidants. Notably, silver trifluoroacetate serves as an unprecedented gaseous CO surrogate in carbonylation reactions, with high purity silver easily recoverable after the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ibuki Nakamura, Ryo Sumitani, Tomoyuki Mochida
Summary: Nitro-nitrito isomerization, a well-known photoreaction in metal complexes, was studied in different packing environments using a cationic platinum(II) nitrito complex. The polymorphs of the salt exhibited various conversion rates at different temperatures, with the beta-form showing a space group change upon photoirradiation. A salt with the (CF3SO2)(2)N- anion displayed both crystalline and glassy states at low temperatures, with the crystalline state showing around 30% conversion at 100 K. Less densely packed crystals in these salts deteriorated upon photoirradiation.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Inorganic & Nuclear
Atsuhiro Miyawaki, Kazuo Eda, Tomoyuki Mochida, Takahiro Sakurai, Hitoshi Ohta, Takahito Nakajima, Kazuyuki Takahashi
Summary: The temperature-dependent study of magnetic susceptibility revealed a change in the spin-crossover transition behavior from abrupt to gradual conversions, with a recovery of the initial abrupt transition at room temperature. Variable-temperature crystal structures showed an SCO-triggered isomerization and relaxation of the azobenzene ligand, indicating a pedal-like motion of the ligand in the high-spin state but not in the low-spin state.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Tomoyuki Mochida, Syou Maekawa, Ryo Sumitani
Summary: A study was conducted to explore ionic liquids with stimuli-responsiveness based on linkage isomerization, resulting in the synthesis of an ionic liquid containing a cationic half-sandwich thiocyanate complex. The N- and S-coordinated isomers showed small solvatochromic absorption shifts in organic solvents, with different solvent dependencies observed for each isomer.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Thi Hien Thuy Nguyen, Chaolu Eerdun, Takuya Okayama, Satoshi Hisanaga, Takumi Tominaga, Tomoyuki Mochida, Jun-ichiro Setsune
Summary: This study discusses bimetallic complexes of hexapyrrole-alpha, omega-dicarbaldimines and their structure-property relationships. The complexes can adopt different structural forms depending on the conformation of the 2,2'-bipyrrole subunit, and reversible oxidation and spectroscopic changes were observed in experimental conditions.
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
(2022)
Article
Chemistry, Multidisciplinary
Hironori Kimata, Takashi Inagaki, Tomoyuki Mochida
Summary: The study compared the phase transitions and crystal structures of four Tf2N salts, all of which exhibited phase transitions at low temperatures with anion ordering. X-ray crystallography revealed that one of the salts had a symmetrical cation structure in the room-temperature phase, but an unsymmetrical structure in the low-temperature phase.
Article
Chemistry, Multidisciplinary
Sok-Yong Choi, Tomoyuki Mochida
Summary: A luminescent ionic liquid containing a cationic rhenium tricarbonyl complex was synthesized, and UV photoirradiation of this liquid in the presence of an organic solvent vapor caused a color change and luminescence quenching via photochemical ligand exchange, enabling the photocontrol of vapochromism.
Article
Chemistry, Inorganic & Nuclear
Shota Hamada, Tomoyuki Mochida
Summary: Ionic liquids containing cationic mixed-valence biferrocenylene derivatives were synthesized, and their melting points and temperature dependence were found to be related to the substituents on the cations.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Ryo Horikoshi, Ryo Sumitani, Natsuko Shimooka, Tomoyuki Mochida
Summary: This study focuses on the crystal structures, absorption wavelengths, and redox potentials of trinuclear complexes formed by ferrocene-based multidentate ligands and various transition-metal salts.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Tomoyuki Mochida, Yi Qiu, Ryo Sumitani, Hironori Kimata, Yoshitomo Furushima
Summary: Several meltable coordination polymers (CPs) with high flexibility and processability have been developed recently. However, the melting mechanism and vitrification conditions of these materials are not fully understood. In this study, meltable CPs incorporating ionic liquid components were synthesized and their crystal structures, melting behaviors, and vitrification upon rapid cooling were investigated.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Ryo Sumitani, Daisuke Kuwahara, Tomoyuki Mochida
Summary: Cationic rhodium complexes with 1,5-cyclooctadiene (cod) ligands were synthesized and their solid-state structures, thermal properties, and reactivities were investigated. The phase transitions of these salts resulted in disordered solid-state structures, with an increase in structural disorder as the cation symmetry decreased. FSA salts showed lower crystal symmetry and less cation disorder compared to SbF6 salts. Additionally, thermal stabilities and reactivities of these salts were studied, revealing different reactions upon melting for FSA and SbF6 salts.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tomoyuki Mochida
Summary: Ionic liquids (ILs) with cationic metal complexes have unique physical properties and chemical reactivities. This review focuses on the molecular design, physical properties, and reactivities of organometallic ILs containing sandwich or half-sandwich complexes. It mainly covers stimuli-responsive ILs that can change their magnetic properties, solvent polarities, colors, or structures by external fields or reaction with coordinating molecules.
Article
Chemistry, Physical
Tomoyuki Mochida, Masato Shimada, Ryo Sumitani
Summary: Controlling the ionic conductivity of liquids is essential for electronic device applications, and we have developed metal-containing ionic liquids that exhibit reversible changes in ionic conductivity through UV photoirradiation and heating. The substituents in these liquids significantly affect the photochemical reaction, and by combining liquids with different reactivity, the conversions can be controlled. The ionic conductivity of these liquids undergoes reversible changes through successive photoirradiation-heating cycles, reflecting their photoreactivity.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Chemistry, Multidisciplinary
Tomoyuki Mochida, Syou Maekawa, Ryo Sumitani
Summary: Cp Ru complexes can be synthesized into Ru-containing ionic liquids (ILs) that exhibit diverse physical and chemical properties depending on the auxiliary ligand. These ILs can undergo in situ ligand exchange, allowing for interconversions between different ligands.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tomoyuki Mochida, Yi Qiu, Yusuke Funasako, Makoto Inokuchi, Mariko Noguchi, Hiroki Fujimori, Yoshitomo Furushima
Summary: A 2D coordination polymer containing an ionic liquid was synthesized via a solvent-free reaction. The material exhibited unique melting properties and underwent solid-liquid phase transitions at different temperatures. Rapid cooling resulted in complete vitrification.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Ryo Sumitani, Masamichi Yamanaka, Tomoyuki Mochida
Summary: In this study, we developed organometallic compounds that release low-molecular-weight gelators upon photoirradiation, and successfully achieved photogelation of ionic liquids. The gelled ionic liquids underwent reversible reaction upon heating, and the photogelation was repeatable for ILs with coordinating cations.
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)
