Article
Chemistry, Organic
Kena Zhang, Olivier Provot, Mouad Alami, Christine Tran, Abdallah Hamze
Summary: This study demonstrates the successful synthesis of various di- and tri-substituted alkenes with high chemoselectivity using N-tosylhydrazones and benzylic phosphates as electrophilic partners. The new catalytic system consisting of PdCl2(CH3CN)(2)/dppp, LiOtBu, and cyclopentyl methyl ether as the solvent exhibits good yields. Furthermore, gram-scale transformations and subsequent postfunctionalization of key intermediates are also reported in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Mohsen Khataminejad, Najmeh Nowrouzi, Dariush Saberi
Summary: In this study, a novel and efficient one-pot tandem synthesis of 2,4,5-tri- and 1,2,4,5-tetra-substituted imidazoles is described. Benzil is first formed via benzoin condensation catalyzed by N-heterocyclic carbene and in situ aerobic oxidation. It then reacts with another aldehyde and ammonium acetate (or amine) to produce the polysubstituted imidazole. The reaction proceeds smoothly in high yield and short reaction time in ethanol as a green solvent, showing high functional group tolerance and avoiding the need for ligands and reducing agents.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhuo Chen, Xiao-Di Nie, Jian-Ting Sun, Ai-Mei Yang, Bang-Guo Wei
Summary: The Zn(OTf)(2)-catalyzed hydroamination of ynamides with aromatic amines has been developed, allowing for the synthesis of various substituted amidine compounds with moderate to excellent yields and high regioselectivities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Vishwas G. Chandrashekhar, Wolfgang Baumann, Matthias Beller, Rajenahally Jagadeesh
Summary: Efficient and general methods for the synthesis of amines using a homogeneous nickel catalyst for hydrogenative cross coupling have been reported. Over 230 functionalized and structurally diverse amines, including pharmaceutically relevant and chiral products, were synthesized using this method.
Article
Chemistry, Inorganic & Nuclear
Shu-Fen Bai, Xiu-Mei Du, Wen-Jing Tian, Hang Xu, Ru-Fen Zhang, Chun-Lin Ma, Yan-Lan Wang, Shuang Lu, Qian-Li Li, Yu-Long Li
Summary: In this study, a series of tertiary phosphine substituted Fe/Se carbonyls were successfully prepared and their synthesis and properties were extensively studied. Some of the compounds showed catalytic activity for the H2 evolution reaction under electrochemical conditions.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Physical
Debopam Sinha, Sudip Biswas, Madhurima Das, Avishek Ghatak
Summary: This study presents an eco-compatible, mild, and operationally simple aqueous phase protocol for the synthesis of 2,4,5-trisubstituted imidazoles using supported Au nanoparticles with high substrate scope. The catalyst can be recovered and reused without significant loss, and the utility of this protocol was further demonstrated in the synthesis of fused and structurally versatile imidazoles. Computational studies were also used to confirm the synthetic attributes of imidazoles. The low E-factor and process mass intensity make this method more sustainable compared to previous literature reports.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Organic
Yuki Naganawa, Kei Sakamoto, Yumiko Nakajima
Summary: This study reports a new method for the selective methylation of chlorosilanes by palladium-catalyzed cross-coupling reaction with organoaluminum reagents.
Article
Chemistry, Organic
Khadra Alomari, N. Sai Pavan Chakravarthy, Bastien Duchadeau, Kristaps Ermanis, Paul A. Clarke
Summary: In this study, omega-unsaturated alcohols were transformed into tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity through alkene metathesis and chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization. DFT calculations and kinetic isotope studies provided insights into the mechanism and origin of enantioselectivity, with excellent agreement between computational and synthetic investigations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Fu-Yu Li, Bei Wang, Hong Xu, Yao Xiao, Dong-Wei Huang, Ji-Yu Wang
Summary: The convenient synthesis of diverse and complex poly-substituted beta-alkenyl valerolactones is achieved through Fe(iii)-catalyzed reduction radical tandem strategy of 2,3-dienoates and allyl alcohols. The allyl alcohols can undergo simultaneous transformations into alkyl radicals and allyl ester intermediates under Fe(iii) catalysis, which then react via Michael addition to form the desired products. Notably, this method also enables the preparation of spiro-valerolactones and cyclo-valerolactones, as well as the transformation of beta-alkenyl valerolactones into previously unreported pyrazole lactone compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Chuan-Jin Hou, Alexander W. Schuppe, James Levi Knippel, Anton Z. Ni, Stephen L. Buchwald
Summary: A method for stereoselective hydroalkenylation of alkynes using enol triflates was reported in this study. The formation of Z,Z- or Z,E-1,3-dienes with excellent stereoselectivity and yield was achieved by leveraging an in situ-generated and geometrically pure vinyl-Cu(I) species. This approach allowed for the synthesis of highly substituted Z-dienes, including pentasubstituted 1,3-dienes, which are challenging to prepare using existing methods.
Article
Chemistry, Organic
Linlin Zhang, Lin Qi, Hui-Jie Du, Jia-Li Liu, Tong-Yang Cao, Zhi-Min Yan, Wei Li, Li-Jing Wang
Summary: A new synthetic method using palladium as catalyst has been developed to efficiently produce 4-methylene-1,3-oxazine frameworks. The conversion of these frameworks to compounds with diverse heteroatom-rich moieties has been demonstrated through subsequent reactions. This method has significant applications in medicinal and biological chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Subin Yoon, Sungbin Lee, Seung Hyun Nam, Hyejeong Lee, Yunmi Lee
Summary: This study presents an efficient and mild method for the synthesis of cyclic beta-amino ketones containing N-substituted quaternary carbon centers through the aza-Michael addition reaction of pyrazoles to beta-substituted cyclic alpha,beta-enones catalyzed by KOt-Bu. A wide range of new and versatile beta-pyrazolyl ketones were obtained in good yields. Additionally, the KOt-Bu-catalyzed one-pot diamination of a cyclic dienone with pyrazoles via aza-1,6-conjugate addition followed by aza-1,4-conjugate addition was explored.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Maxime Hourtoule, Laurence Miesch
Summary: We developed a domino reaction for the synthesis of 2-amido-5-fluoropyrroles from CF3-substituted N-allenamides. By employing silver catalysis with a primary amine, the in situ generated gem-difluorinated ene-ynamides derived from CF3-substituted N-allenamides undergo simultaneous hydroamination and 5-endo-trig addition/beta-fluoride elimination sequence, leading to the construction of 2-amido-5-fluoropyrroles. This method shows excellent functional group compatibility and can be used for the synthesis of functionalized benzo-oxazoles by using 2-aminophenols.
Article
Chemistry, Organic
Woo-Ok Jung, Minjin Yoo, Madyson M. Migliozzi, Jason R. Zbieg, Craig E. Stivala, Michael J. Krische
Summary: In this study, it was shown that modified cyclometalated pi-allyliridium catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates with high levels of enantioselectivity and complete branched regioselectivities, despite the formation of more highly substituted C-N bonds.
Article
Chemistry, Applied
Zhong-Yi Li, Peng-Yu Zhu, Han Chang, Zhen-Zhu Hou, Mei-Ling Shao, Bin Zhai
Summary: The fluorescence sensing properties of two three-dimensional metal-organic frameworks (MOFs) were investigated, and they exhibited high sensitivity and selectivity towards Fe3+, MnO4- and Cr2O72-. The MOFs showed good stability and recircularity.
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)