Article
Chemistry, Inorganic & Nuclear
Nazaret Santamaria, Clara Velasco, Mario Marin, Celia Maya, M. Carmen Nicasio
Summary: In this study, a series of LPdCl2(amine) complexes bearing dialkylterphenyl phosphanes (PR2Ar ') and pyridine or morpholine ligands were synthesized and characterized. These novel compounds were tested as precatalysts in aryl amination reactions. The complex [(PCyp(2)Ar(Xyl2))PdCl2(morpholine)] exhibited the best catalytic activity, enabling the room-temperature coupling of aryl bromides and chlorides with aniline.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Physical
Philippe Steinsoultz, Aurelien Bailly, Patrick Wagner, Estefania Oliva, Martine Schmitt, Laurence Grimaud, Frederic Bihel
Summary: This study presents an efficient Buchwald-Hartwig crosscoupling reaction in alcoholic solvent, where a low catalyst loading exhibited excellent performance. Mechanistically, extremely bulky biarylphosphine ligands interact with the dimeric precatalyst to form active catalysts in situ, with alcoholic solvents playing a prominent role in the formation of the active catalyst.
Article
Chemistry, Inorganic & Nuclear
Yu-Cheng Hsu, Ming-Tsz Chen
Summary: The N-heterocyclic carbene-palladium(II) amine complexes synthesized in this study showed good catalytic activities for the Buchwald-Hartwig amination reaction of aryl chlorides, yielding 21 expected coupling products in moderate to high yields under mild conditions. The complexes were characterized by single crystal X-ray diffraction and NMR spectroscopy, and the reactions were conducted in air without purification of starting materials.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zi-Chao Wang, Yan-Yu Li, Shuo-Qing Zhang, Xin Hong, Shi-Liang Shi
Summary: This article reports a highly efficient nickel catalyst for the arylation of sterically hindered primary and secondary amines with aryl chlorides or phenol derivatives, enabled by an unsymmetric N-heterocyclic carbene ligand. The method is general, efficient, and scalable, providing excellent yields of various sterically demanding anilines under mild conditions. Computational studies suggest that the unsymmetric bulky and flexible N-heterocyclic carbene ligand plays a critical role in balancing the oxidative addition and reductive elimination steps.
Article
Chemistry, Multidisciplinary
Christian M. Heckmann, Francesca Paradisi
Summary: The combination of biocatalysis and chemocatalysis can provide a powerful method for accessing chiral N-aryl amines in excellent enantioselectivity. The use of a bi-phasic buffer-toluene system and the ligand GPhos allows for a telescoped cascade with up to 89% overall conversion in the presence of excess alanine, without observed coupling to alanine.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Bingbing Sheng, Cuicui Zeng, Jing Chen, Wen-Cai Ye, Wei Tang, Ping Lan, Martin G. Banwell
Summary: Two distinct and concise syntheses of zephycandidine A (1) from readily available starting materials were reported in this paper. Preliminary biological screening of compounds 1, 10 and certain precursors showed some possess anti-viral properties but are not notable inhibitors of acetylcholinesterase.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hua-Wei Liu, Peng He, Wen-Tao Li, Wei Sun, Kai Shi, You-Qin Wang, Qian-Kun Mo, Xin-Yu Zhang, Shou-Fei Zhu
Summary: The application of computational tools in catalyst design has been limited due to the neglect of mechanistic data. In this study, we propose a new catalyst design strategy, catalyst-oriented design based on elementary reactions (CODER), which combines computational tools with researcher experience and fully utilizes mechanistic data. By using CODER, highly efficient Pd catalysts for C-N coupling were developed, significantly improving the synthesis efficiency of widely used triarylamine optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tian Cao, Yi-Peng Luo, Long Cheng, Jia-Li Zhao, Qiao-Sen Jia, Shu Zhang, Xiang-Wei Liu
Summary: This article describes a novel method for the de novo catalytic synthesis of diarylamines through a palladium-catalyzed reductive Buchwald-Hartwig amination of nitroarenes with aryl (pseudo)halides. The use of upstream nitroarenes as arylamine surrogates, the choice of bis(pinacolato)diboron (B(2)pin(2)) as a stoichiometric reducing agent, and the wide scope of substrates including (hetero)aryl halides (Cl, Br, and I) and aryl triflates are the notable features of this protocol. Furthermore, its successful application in the synthesis of advanced intermediates and active pharmaceutical ingredients provides an alternative and cost-effective approach to the synthesis of diarylamine-incorporated molecules. Preliminary mechanistic investigations suggest the involvement of amine and nitrosoarene intermediates in this reductive process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Jie Xu, Cheol K. Chung, Andrew McClory, Kyle A. Mack, Michael E. Dalziel, Alec Fettes, Kyle Clagg, Ngiap-Kie Lim, Georg Wuitschik, Christian Jenny, Laure Finet, Michael Kammerer, Haiming Zhang, Remy Angelaud, Francis Gosselin
Summary: GDC-9545, a selective estrogen receptor degrader, is being developed as a treatment for ER+/HER2- breast cancer. A robust and efficient manufacturing process has been developed to produce GDC-9545.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Applied
Fritz Bliss, Serena Fantasia, Erwann Le Coz, Kurt Puntener
Summary: An efficient palladium-catalyzed coupling method using ethanol as a solvent was developed for the streamlined synthesis of a lead candidate for schizophrenia treatment. The use of Xantphos ligand was found to be crucial in preventing common side reactions. The scope of the methodology was thoroughly investigated and presented.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Volodymyr Semeniuchenko, Sepideh Sharif, Jonathan Day, Nalin Chandrasoma, William J. Pietro, Jeffrey Manthorpe, Wilfried M. Braje, Michael G. Organ
Summary: (DiMeIHept(Cl))Pd, a hyper-branched N-aryl Pd NHC catalyst, is efficient at performing amine arylation reactions in solvent-free conditions, allowing for the synthesis of various aniline derivatives, including those containing alcohol moieties, on a multi-gram scale.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Benjamin R. Trowse, Fergal P. Byrne, James Sherwood, Peter O'Brien, Jane Murray, Thomas J. Farmer
Summary: Buchwald-Hartwig amination is a crucial method for synthesizing N-arylamines, and using 2,2,5,5-tetramethyloxolane as a solvent can provide significant advantages over toxic toluene, especially for electron-deficient aryl bromides.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Physical
Victor Wambua, Jennifer S. Hirschi, Mathew J. Vetticatt
Summary: This study introduces a practical approach for the rapid determination of C-13 kinetic isotope effects using a designed reactant with two identical reaction sites. By investigating and evaluating the mechanism under different synthetic conditions, it offers an efficient technique for rapidly obtaining high-resolution information regarding the transition structure of synthetically relevant reactions.
Article
Chemistry, Organic
Junxin Rao, Xiaoyu Ren, Xin Zhu, Zhen Guo, Chengming Wang, Cong-Ying Zhou
Summary: In this study, a Ru(ii)-catalyzed C-N cross-coupling reaction of diazoquinones with arylamines was reported, providing access to functionalized diarylamines with high yields under mild and neutral conditions. The synthetic utility of this method was demonstrated by the modular synthesis of structurally sophisticated diarylamine derivatives and the short synthesis of an anti-inflammatory compound.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yaxu Liu, Vladislav A. Voloshkin, Thomas Scattolin, Min Peng, Kristof Van Hecke, Steven P. Nolan, Catherine S. J. Cazin
Summary: A synthetic procedure for preparing stable [Pd(NHC)Cl-2(DMS/THT)] pre-catalysts was reported, and their catalytic activity was studied in Buchwald-Hartwig and Suzuki-Miyaura reactions. The synthesized complexes exhibited higher catalytic activity and were considered as greener alternatives to classical PEPPSI type catalysts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Takao Osako, Jakkrit Srisa, Kaoru Torii, Go Hamasaka, Yasuhiro Uozumi
Article
Chemistry, Organic
Hao Hu, Hajime Ota, Heeyoel Baek, Kenta Shinohara, Toshiaki Mase, Yasuhiro Uozumi, Yoichi M. A. Yamada
Article
Chemistry, Physical
Heeyoel Baek, Keiichiro Kashimura, Takashi Fujii, Shuntaro Tsubaki, Yuji Wada, Shigenori Fujikawa, Takuma Sato, Yasuhiro Uozumi, Yoichi M. A. Yamada
Article
Chemistry, Multidisciplinary
Shota Mizuno, Hiroaki Tsuji, Yasuhiro Uozumi, Motoi Kawatsura
Article
Chemistry, Applied
Aya Ohno, Takuma Sato, Toshiaki Mase, Yasuhiro Uozumi, Yoichi M. A. Yamada
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Raghu N. Dhital, Abhijit Sen, Takuma Sato, Hao Hu, Rikako Ishii, Daisuke Hashizume, Hikaru Takaya, Yasuhiro Uozumi, Yoichi M. A. Yamada
Article
Chemistry, Organic
Anggi Eka Purta, Shun Ichii, Aya Tazawa, Yasuhiro Uozumi
Article
Chemistry, Multidisciplinary
Seitaro Koshino, Shusuke Hattori, Shota Hasegawa, Naoki Haraguchi, Takeshi Yamamoto, Michinori Suginome, Yasuhiro Uozumi, Yujiro Hayashi
Summary: The immobilization of diphenylprolinol silyl ether on solid supports allows for easy recycling and reusability. While polymer-supported organocatalysts generally exhibit decreased reactivity compared to monomer catalysts, diphenylprolinol anthryl-methyl ether supported on PS-PEG resin was found to be a highly reactive organocatalyst, demonstrating excellent diastereo- and enantioselectivities in the Michael reaction of aldehyde and nitroalkene in water without the presence of organic solvents.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Inorganic & Nuclear
Heeyoel Baek, Takuma Sato, Yasuhiro Uozumi, Yoichi M. A. Yamada
Summary: Highly reusable and active silicon-nanowire-array-stabilized metal-nanoparticle (SiNA-MNP) catalysts have been prepared for effective hydrogenation under mild conditions. Monometallic and bimetallic nanoalloy catalysts were synthesized without the need for a reducing agent or other external factors, showing robust stability and high reusability. Characterization of the catalysts was conducted using various techniques, and the catalytic activity was evaluated through hydrogenation of trans-stilbene in a hydrogen atmosphere.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shuichi Hirata, Takao Osako, Yasuhiro Uozumi
Summary: A new palladium-catalyzed method for aminocarbonylation of aryl halides was developed, using formamide acetals as amino carbonyl sources under neutral conditions. The method showed good tolerance towards a wide range of functional groups on the substrates, making it applicable for the synthesis of various organic compounds.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Organic
Shintaro Okumura, Yasuhiro Uozumi
Summary: A new photocatalytic umpolung reaction has been developed for the generation of anionic carbinol synthons from aromatic aldehydes or ketones, which are then used to produce alpha-hydroxycarboxylic acids through nucleophilic addition to electrophilic carbon dioxide under visible light irradiation.
Article
Chemistry, Organic
Toshimasa Suzuka, Ryoko Niimi, Yasuhiro Uozumi
Summary: A cyanide-free aromatic cyanation was achieved using nitromethane as a cyanide source, with a palladium catalyst supported by an amphiphilic polystyrene-poly(ethylene glycol) resin, and an alkyl halide acting as a reagent. The process involves a palladium-catalyzed cross-coupling of an aryl halide with nitromethane followed by the transformation of the intermediate into a nitrite using 1-iodobutane.
Article
Chemistry, Organic
Misa Kawase, Kyosuke Matsuoka, Tsutomu Shinagawa, Go Hamasaka, Yasuhiro Uozumi, Osamu Shimomura, Atsushi Ohtaka
Summary: This study utilized PS-PdONPs as a catalyst for the Suzuki-Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water, achieving high yields and demonstrating the catalyst's ability for multiple cycles of reuse.
Article
Chemistry, Organic
Keisuke Minami, Maki Minakawa, Yasuhiro Uozumi
Summary: The reaction of 2,2'-dithiobis(benzenamine)s with various aldehydes in the presence of CuOAc catalyst under air without any additives yielded the corresponding benzothiazoles. When cycloalkylcarbaldehydes were reacted under similar conditions, benzothiazoles and heterocyclic spiro compounds were produced. Gram-scale preparation was successfully carried out under open-flask conditions in the presence of CuOAc catalyst.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Raghu N. Dhital, Abhijit Sen, Hao Hu, Rikako Ishii, Takuma Sato, Yoko Yashiroda, Hiromi Kimura, Charles Boone, Minoru Yoshida, Yushi Futamura, Hiroyuki Hirano, Hiroyuki Osada, Daisuke Hashizume, Yasuhiro Uozumi, Yoichi M. A. Yamada
Summary: In this study, a phenylboronic ester-activated aryl iodide-selective Buchwald-Hartwig-type amination was developed. The reaction proceeds smoothly to afford the corresponding amines in high yields in the presence of phenylboronic ester. A wide variety of aryl iodides can be applied, while aryl chlorides and bromides remain intact. The reaction is catalyzed by the phenylboronic ester and shows potential antifungal activity.
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)
