Article
Chemistry, Organic
Suresh Kanikarapu, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: This study presents a straightforward and selective intramolecular cyclization reaction for the synthesis of diverse compounds. The reaction exhibits broad functional group compatibility, leading to improved synthetic efficiency and yield of the products.
Article
Chemistry, Organic
Yingjian Ren, Zhanglang Zhou, Weinan Chen, Si Liu, Min Wang, Gang Zhou
Summary: In this study, unexpected 6-endo-dig and ring-expansion cycloisomerizations were discovered for ortho-disubstituted thiophene derivatives with 1-en-3-yne moieties in the presence of PtCl2. The reaction pathway was found to be determined by the substrate structure. A benzo[b]thiophene derivative was obtained through a 6-endo-dig cyclization with a [1,2]-alkyl shift when the CvC double bond belonged to an aromatic ring, while a ring-expansion cyclization reaction occurred when the double bond came from an aliphatic alkene, resulting in a cyclopenta[c]thiapyran analogue. The proposed mechanisms of both reactions were verified by density functional theory calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Honghua Zuo, Hendrik F. T. Klare, Martin Oestreich
Summary: A catalytic silylium-ion-promoted intramolecular alkyne carbosilylation reaction is reported, involving electrophilic activation of the C-C triple bond by a silylium ion and maintenance of the catalytic cycle through protodesilylation of an allylsilane reagent. The reaction exhibits exclusive 7-endo-dig selectivity and results in fully substituted vinylsilane derivatives of silylated benzocycloheptenes. Control experiments demonstrate that the catalytically active silylium ion can be regenerated by protodesilylation of the vinylsilane product.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Tales A. C. Goulart, Ana M. S. Recchi, Davi F. Back, Gilson Zeni
Summary: The Lewis acid-promoted cyclization reaction of benzomidazole thiols with propargyl alcohols for the selective synthesis of benzoimidazolo thiazines and benzothiazolo imidazoles is described. The reaction is regioselective and controlled by the choice of solvent. The best reaction conditions were determined through systematic study, resulting in the formation of six-membered benzoimidazolo thiazines using boron trifluoride etherate and dichloromethane as the solvent, and five-membered benzothiazolo imidazoles using the same starting material and reagents with dimethylformamide as the solvent. The proposed mechanism of the cyclization reaction is based on experimental results and control experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Chanhyun Jung, Siyuan Li, Kwanghee Lee, Mayavan Viji, Heesoon Lee, Soonsil Hyun, Kiho Lee, Young Kee Kang, Chhabi Lal Chaudhary, Jae-Kyung Jung
Summary: In this study, solvent-directed intramolecular hydrofunctionalization of readily available o-alkynoylphenols was successfully achieved under reagent-free conditions. The strategy is remarkable for its regioselectivity, atom economy, and efficiency in terms of atom, carbon, and reaction mass.
Article
Chemistry, Organic
Roberto do Carmo Pinheiro, Luiz Eduardo Welter, Bernardo A. Iglesias, Davi F. Back, Luiza Souza Marques, Cristina Wayne Nogueira, Gilson Zeni
Summary: Heterocycles fused to seven-membered rings were synthesized in a highly selective manner using potassium tert-butoxide-catalyzed one-pot cyclization. Systematic study revealed that a catalytic amount of potassium tert-butoxide, dimethyl sulfoxide, and the tert-BuOK/tert-BuOH equilibrium played crucial roles in the formation of products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yi-En Liang, Ming-Yiang Chang, Hsi Ho, Chun-Tang Chiou, Balaji D. Barve, Wen-Tai Li
Summary: A novel cascade reaction utilizing Pd-(II) catalysis was developed for the synthesis of fused oxatricyclic compounds from 2-benzyl-3-alkynyl chromones and activated/unactivated alkenes. This concise one-pot synthetic approach offers potential in difunctionalizing unbiased alkynes based on 2-benzyl-3-(alkynyl)-4H-chromen-4-one via O-attack endo-dig cycloisomerization followed by olefination with both activated and unactivated alkenes.
Article
Chemistry, Multidisciplinary
Gottam Sreenivasulu, Veerabhushanam Kadiyala, Chittala Emmaniel Raju, Balasubramanian Sridhar, Galla Karunakar
Summary: An efficient gold-catalyzed synthesis of pyrazolo[1,5-a]pyridines has been developed from pyrazolo substituted propargyl alcohols via 6-endo-dig cyclization. In this intramolecular cyclization reaction, a new C-N bond was regioselectively formed, and good to excellent yields of pyrazolo[1,5-a]pyridines were obtained in one-pot.
Article
Chemistry, Applied
Peng Ma, Jianhui Wang, Guiyan Liu
Summary: In this paper, a simple method for the synthesis of substituted 1-naphthylamines is described. The method involves a Cu(I) catalytic system in water, avoiding competitive reactions and allowing for the rapid synthesis of a diverse compound library. Gram-scale synthesis and mechanism studies further demonstrate the synthetic potential and reaction process of this method.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ping Wu, Liandi Wang, Kaikai Wu, Zhengkun Yu
Summary: This study addresses the challenge of the direct synthesis of triazole 2-oxides in the field of N-heterocyclic chemistry. By utilizing a novel copper-catalyzed nitrosylation/annulation cascade of enaminones and using noncorrosive tert-butyl nitrite, the synthesis of 1H-1,2,3-triazole 2-oxides with wide substrate scopes and good tolerance to various functional groups is achieved.
Article
Chemistry, Organic
Rattana Worayuthakarn, Sirikan Deesiri, Kittipong Chainok, Nanthawat Wannarit, Somsak Ruchirawat, Nopporn Thasana
Summary: A highly regioselective divergent approach for synthesizing phosphine-containing indane/indene derivatives from ene-yne-oxazolone precursors was reported, along with proposed reaction mechanism. The protocol utilized H-phosphonate as reagent in a silver-catalyzed or base-mediated cyclization to construct the corresponding compounds in good yields (up to 88%).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mou Mandal, Renuka Pradhan, Upakarasamy Lourderaj, Rengarajan Balamurugan
Summary: A direct ring-closing strategy using vinylogous amides under gold catalysis has been developed to synthesize benzo[b]azepines, overcoming the traditional 5-endo-dig cyclization. Deuterium scrambling experiments and DFT studies support a reaction mechanism involving a stabilizing conformational change of a seven-membered vinyl gold intermediate through a key cyclopropyl gold carbene intermediate and subsequent protodeauration mediated by the counter anion.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rajendra K. Mallick, Shubham Dutta, Manash Protim Gogoi, Akhila K. Sahoo
Summary: This study demonstrates a method for keteniminium triggered dienone-phenol rearrangement using a combination of gold catalyst and ynamide to form the keteniminium species in situ. The transformation allows for the synthesis of compounds with a specific structure through intramolecular proton transfer to vinylic gold species.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Ryo Murakami, Hiroto Tanishima, Daisuke Naito, Hikari Kawamitsu, Ryoya Kamo, Ayaka Uchida, Kazuki Kawasaki, Chihiro Kiyohara, Motoki Matsuo, Kakeru Maeda, Fuyuhiko Inagaki
Summary: The study synthesized a cationic catalyst Au(DPB)X-3 with a specific ligand, which was successfully utilized in a specific reaction of yne-indoles.
TETRAHEDRON LETTERS
(2021)
Correction
Chemistry, Multidisciplinary
Hassan Seyrani, Sorour Ramezanpour, Aref Vaezghaemi, Farzad Kobarfard
Summary: The correction presents a novel reaction sequence for the selective synthesis of saccharin substituted 2,5-dihydropyrroles via sequential Ugi-Smiles reaction and transition-metal-free endo-dig Conia-ene cyclization.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Xiaohan Ye, Chenhuan Wang, Shuyao Zhang, Jingwen Wei, Chuan Shan, Lukasz Wojtas, Yan Xie, Xiaodong Shi
Article
Chemistry, Organic
Ye Wang, Lei Zheng, Xiaodong Shi, Yunfeng Chen
Summary: In this study, successful 1,3-difunctionalization of beta-alkylsubstituted nitroalkenes was achieved through a synergistic Lewis base catalysis and TBHP radical oxidation, yielding vinylic alkoxyamines in good to excellent yields. This work further extends the general synthetic application of beta-alkyl nitroalkenes.
Article
Chemistry, Multidisciplinary
Teng Yuan, Qi Tang, Chuan Shan, Xiaohan Ye, Jin Wang, Pengyi Zhao, Lukasz Wojtas, Nicholas Hadler, Hao Chen, Xiaodong Shi
Summary: This study presents a novel method for alkyne trifunctionalization through gold catalysis, achieving consecutive reactions with high efficiency and excellent yields under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Kai Zhao, Ying He, Chuan Shan, Lukasz Wojtas, Junyu Ren, Yu Yan, Hanzhong Shi, Haonan Wang, Zhiguang Song, Xiaodong Shi
Summary: A helical metal-organic framework with significantly improved air and moisture stability was successfully prepared using a new ligand design, providing a new strategy for porous material constructions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Teng Jia, Shengyu Fan, Fengmian Li, Xiaohan Ye, Wenke Zhang, Zhiguang Song, Xiaodong Shi
Summary: The intermolecular hydro-amination of arylalkynes with aliphatic amine catalyzed by a combination of 1,2,3-triazole-coordinated gold(I) catalyst and Zn(OTf)(2) cocatalyst has been successfully achieved with good to excellent yields and regioselectivity. Compared to previous methods, this approach offers an alternative catalyst system for this fundamental chemical transformation with high efficiency and practical conditions.
Article
Chemistry, Multidisciplinary
Xiaohan Ye, Chenhuan Wang, Shuyao Zhang, Qi Tang, Lukasz Wojtas, Minyong Li, Xiaodong Shi
Summary: This study achieved enantioselective, intermolecular alkene arylamination through gold redox catalysis. Chiral P,N ligands were found to be the optimal choice, enabling alkene aminoarylation with good yields and excellent stereoselectivity. As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage and introduced a new way to conduct gold redox catalysis with stereochemistry control.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Zhuo Wang, Xiaohan Ye, Meina Jin, Qi Tang, Shengyu Fan, Zhiguang Song, Xiaodong Shi
Summary: 4-Aminobenzotriazole (ABTA) was used for the first time as an effective removable directing group (DG) in Pd-catalyzed C-H activation. Compared to commonly used pyridine and quinoline analogs, ABTA exhibited significantly improved reactivity and achieved aerobic oxidative C-H olefination in excellent yields. Additionally, ABTA was easily removed under mild conditions, making it a promising directing group for macrocyclization reactions.
Article
Chemistry, Multidisciplinary
Teng Yuan, Kelton Radefeld, Chuan Shan, Carter Wegner, Erin Nichols, Xiaohan Ye, Qi Tang, Lukasz Wojtas, Xiaodong Shi
Summary: Here, we have reported an intermolecular asymmetric hydrative aldol reaction by using a vinyl-gold intermediate under ambient conditions. This reaction provides a base-free approach to β-hydroxy amides with high efficiency, yielding up to 95% and with over 50 examples. The use of vinyl gold intermediate as a reactive nucleophile and Fe(acac)(3) as a critical co-catalyst prevents undesired protodeauration, allowing the transformation to proceed under mild conditions with excellent functional group tolerance and stereoselectivity (>20:1 d.r. and up to 99% ee).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jingwen Wei, Yangyang Xing, Xiaohan Ye, Bao Nguyen, Lukasz Wojtas, Xin Hong, Xiaodong Shi
Summary: In this study, a new synthetic strategy for enantioselective 1,2-dihydropyridine synthesis was reported. Using the gold-catalyzed intermolecular condensation of amine and diyne-ene, the synthesis was achieved through a formal [3+2+1] fashion with up to 95% yield and up to 99% enantiomeric excess (e.e.).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Chenhuan Wang, Shuyao Zhang, Teng Yuan, Abiola Azee Jimoh, Maxwell Abreu, Chuan Shan, Lukasz Wojtas, Yangyang Xing, Xin Hong, Xiaodong Shi
Summary: Triazole-ruthenium carbene complexes (TA-Rus) are a new class of modified Grubbs catalysts that can achieve challenging olefin metathesis at higher temperatures without decomposition. Compared to previously reported N-tethered Ru-carbene complexes, TA-Ru complexes have higher reactivity and can be used for cross-metathesis, ring-closing metathesis, and dynamic covalent chemistry reactions.
Article
Chemistry, Multidisciplinary
Mengjia Liu, Ying He, Lukasz Wojtas, Xiaodong Shi
Summary: In this study, a recyclable isoG-star material was developed for selective extraction of Cs+, demonstrating good reusability. This new supramolecular macrocycle offers a practical platform for the environmentally friendly and highly effective treatment of radiocesium.
Article
Chemistry, Organic
Jingwen Wei, Mengjia Liu, Xiaohan Ye, Shuyao Zhang, Elaine Sun, Chuan Shan, Lukasz Wojtas, Xiaodong Shi
Summary: The styryl dehydro-Diels-Alder reaction with a conjugated diyne is reported, which allows for effective transformation under milder conditions and produces high yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Mengjia Liu, Ying He, Chuan Shan, Lukasz Wojtas, Ion Ghiviriga, Omar Fathalla, Yu Yan, Xiaopeng Li, Xiaodong Shi
Summary: Systematic investigations were conducted on the effects of various substituted groups at C8 purine and ribose on pentaplex formation. Modification on ribose with the deoxy isoG derivative showed better assembly with Cs+ cation. Solvent and anion effects were found to play a critical role in the formation of stable isoG pentaplexes.
Article
Chemistry, Multidisciplinary
Yanbin Zhang, Ying He, Lukasz Wojtas, Xiaodong Shi, Hao Guo
CELL REPORTS PHYSICAL SCIENCE
(2020)
Article
Chemistry, Multidisciplinary
Jingyang Li, Ying He, Li Wang, Guanghua Li, Yongcun Zou, Yan Yan, Dandan Li, Xinli Shi, Zhiguang Song, Xiaodong Shi
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)
