Article
Chemistry, Organic
Ruiting Yang, Qiumin Xie, Qian Yan, Xiuli Zhang, Bao Gao
Summary: A novel method for synthesizing thioesters using S-aryl thioformates as sources has been reported. The reaction achieved desirable yields of thioesters with various substrates under mild conditions. Gram-scale synthesis was also successful using this method.
Article
Chemistry, Organic
Ruiting Yang, Qiumin Xie, Qian Yan, Xiuli Zhang, Bao Gao
Summary: A novel approach for synthesizing thioesters using S-aryl thioformates as sources was reported, showing smooth transfer of the thioester moiety to aryl iodides. The reaction can be conducted at ambient temperature and tolerates a variety of substrates, with moderate to excellent yields. The scalability of this method was demonstrated through a gram-scale reaction with little change in chemical yield.
Article
Chemistry, Organic
Brett Andrew Hopkins, Blane Zavesky, Derick White
Summary: This paper describes a palladium-catalyzed cross-coupling reaction of thioacetates and aryl halides. Through screening, a unique catalyst was discovered, which allowed for high yields of the desired products under mild reaction conditions. The method offers accessible starting materials and a wide range of reactions, demonstrating its significance in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Brett Andrew Hopkins, Blane Zavesky, Derick White
Summary: In this study, a palladium-catalyzed cross-coupling reaction between thioacetates and aryl halides is described. The use of a specific catalyst resulted in high yields of thioarene products under mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Hiroki Miura, Tomoya Toyomasu, Hidenori Nishio, Tetsuya Shishido
Summary: A gold-catalyzed thioetherification of C(sp(3))-O bonds is reported, using allyl phosphates and thiosilanes as substrates. The reaction proceeds efficiently under mild conditions, providing the corresponding allyl sulfides with excellent yields. The study also demonstrates the thioetherification of C-O bonds in benzyl and propargyl phosphates, as well as the high enantiomeric purity achieved in the reaction of an optically active benzyl phosphate. Soluble gold species are identified as the responsible catalysts, with cationic gold species on ZrO2-supported gold nanoparticles serving as the active catalytic species.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Organic
Alec H. Christian
Summary: The metallaphotoredox-catalyzed C-S cross-coupling allows for the formation of biaryl thioethers from heteroaryl bromides and alpha-thioacetic acids. This method facilitates cross-coupling between building blocks containing reactive functional groups, nitrogen heterocycles, and pharmaceutically relevant scaffolds. Mechanistic experiments show a unique pathway for the C-S cross-coupling to occur.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wenjun Miao, Chuanfa Ni, Pan Xiao, Rulong Jia, Wei Zhang, Jinbo Hu
Summary: This novel nickel-catalyzed reductive cross-coupling reaction allows the formation of C(sp(2))-C(sp(2)) bonds through selective C(sp(2))-S bond cleavage, showcasing the new reactivity of 2-PySO2CF2H reagent. The use of readily available nickel catalyst and sulfones as coupling partners enables facile access to biaryls under mild reaction conditions without pregeneration of arylmetal reagents.
Article
Chemistry, Organic
Guifang Chen, Bo Xu
Summary: We have developed a C-O cross-coupling reaction between (hetero)aryliodides and silver carboxylates using a Au-I/Au-III catalytic cycle. This transformation shows exclusive chemoselectivity and is insensitive to moisture and air. It is applicable to both aromatic and aliphatic (including primary, secondary, and tertiary) silver carboxylates, and works well in both intermolecular and intramolecular settings. Importantly, high yields are obtained regardless of the electronic effect and steric hindrance of the substrates.
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xin Fu, Tingting Ran, Yu Zhou, Jie Liu
Summary: Here, a facile and efficient electrochemical promoted Ni-catalyzed reductive carbon-carbon bond formation is reported. This Nicatalyzed modular approach shows good functional group tolerance and broad substrate scope. It enables the synthesis of a series of allylic compounds, including various structurally complex natural products and pharmaceutical motifs.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tianhao Xu, Xingyu Zhou, Xiong Xiao, Yan Yuan, Long Liu, Tianzeng Huang, Chunya Li, Zhi Tang, Tieqiao Chen
Summary: A nickel-catalyzed decarbonylative thioetherification of carboxylic acids with thiols has been developed, enabling the coupling of carboxylic acids with various thiols to produce thioether products. This reaction holds great synthetic value in the modification of bioactive molecules and the synthesis of certain acaricides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Aijie Cai, Wenhao Yan, Wei Liu
Summary: A new catalytic strategy has been developed to activate C-O bonds in alcohol-derived xanthate esters using aryl radicals, allowing for the discovery of the first catalytic deoxygenative difluoromethylation reaction. This approach exhibits a broad substrate scope and functional group tolerance, enabling late-stage modification of complex pharmaceutical agents.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Huan Wang, Yudong Li, Yajun Sun, Yuehui Li
Summary: The first example of catalytic thiocarbonylation of aryliodides using CO2 has been achieved by using a combination of PdCl(2) and carbazole-derived phosphine ligands. Under mild conditions, a broad range of aryl iodides were converted to the desired thioester products in the presence of aryl or alkyl thiols (33 examples, up to 96% yields). The choice of metal, ligands, and reductant was crucial for achieving high efficiency and chemoselectivity. Moreover, this strategy provided an effective method for late-stage functionalization of biorelevant molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jie Wang, Qing -Yang Li, Shan -Shan Wang, Xin-Yan Wu, Xingguang Li, Pei-Nian Liu
Summary: We have reported a novel rhodium-catalyzed rearrangement reaction involving N-substituted 2-thiopyridones and diazoesters. This reaction proceeds through the rhodium-catalyzed formation of sulfur ylides, followed by a direct C-N bond cleavage, achieving N-to-C 1,4-pyridyl migration. The protocol can be used to synthesize various thiopyridines with tetrasubstituted carbon stereocenters in moderate to excellent yields, expanding the transformation pattern of sulfur ylide intermediates in rearrangement reactions.
Article
Chemistry, Organic
Jian-Xing Xu, Le-Cheng Wang, Xiao-Feng Wu
Summary: A palladium-catalyzed desulfonative carbonylation of thiosulfonates has been developed, converting a series of S-aryl/alkyl benzenesulfonothioates to thioesters with high yields by releasing SO2 and inserting CO. The addition of dimethylacetamide (DMAc) as a solvent enhanced the reaction due to its strong ability to absorb SO2.
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)