Article
Chemistry, Multidisciplinary
Tatiana Suarez-Rodriguez, Angel L. Suarez-Sobrino, Alfredo Ballesteros
Summary: Gold(I)-catalyzed higher-order [8+2] cycloadditions of 8-aryl-8-azaheptafulvenes with allenamides and ynamides were studied, resulting in the formation of 1,8-dihydrocycloheptapyrroles and 2-amido-1,4-dihydrocycloheptapyrroles, respectively. The reactions proceeded with good yields and various substituents, suggesting a nucleophilic attack mechanism involving the gold-activated electron-rich moieties of the allenamide and ynamide.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Shivani Arora, Surya Pratap Singh, Parashuram Sharma, Anand Singh
Summary: PTSA-catalyzed reactions using ketene dithioacetals as starting materials enable the efficient synthesis of 3-aryl coumarins and indenes. These reactions proceed under mild conditions without the need for transition metals or oxidants.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Lucas Pages, Maxime Bouquin, Florian Jaroschik, Florian Monnier, Marc Taillefer
Summary: We present a simple protocol for the copper-catalyzed hydrothiolation of N-unsaturated precursors, enabling the room-temperature transformation of thiols into various thioethers and thioaminals with good selectivity. The use of a low loading of commercially available Cu(CH3CN)(4)PF6 catalyst facilitates the process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qing Sun, Jia-Jie Chen, Jia-Yi Liu, Wen-Qing Zhang, Xin Lu, Jin-Heng Li, Ren-Jie Song
Summary: This cutting-edge research work provides a comprehensive theoretical investigation into the mechanism of Au(I)-catalyzed annulations between ynamides and 1,2-benzisoxazoles. The study also explores the chemoselectivity of the reactions in the presence of different ligands and factors influencing the Z/E-configuration of the resulting cyclic products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Long Li, Wen-Feng Luo, Long-Wu Ye
Summary: Gold-catalyzed nitrene-transfer reactions have gained extensive attention for their efficient and rapid synthesis of nitrogen-containing molecules. Recent progress in the gold-catalyzed formal annulations of ynamides with isoxazole derivatives as nitrene-transfer reagents via alpha-imino gold carbenes has shown promise in the atom-economic and rapid construction of N-heterocycles.
Article
Chemistry, Multidisciplinary
Shashank Shandilya, Manash Protim Gogoi, Shubham Dutta, Akhila K. Sahoo
Summary: Ynamide, a unique species with inherited polarization of nitrogen lone pair electron to triple bond, has been widely used for the development of novel synthetic methods and the construction of unusual N-bearing heterocycles. This review provides an overall scenic view into the gold catalyzed transformation of ynamides, including their reactivity towards various transfer reagents and carbon nucleophiles.
Article
Chemistry, Multidisciplinary
Galla V. Karunakar, Chittala Emmaniel Raju, Karra Sai Bhavani Nagasri Himaja, Perla Bharath Kumar, Balasubramanian Sridhar
Summary: N-aryl-1H-pyrazolyl substituted benzenesulfonamide derivatives were regioselectively obtained from ynamides and pyrazoles through silver-catalyzed reaction. In this intermolecular organic transformation, several substituted benzenesulfonamides were obtained in good to excellent yields by forming a new C-N bond under mild reaction conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
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, Multidisciplinary
Ching-Nung Chen, Wei-Min Cheng, Jian-Kai Wang, Tzu-Hsuan Chao, Mu-Jeng Cheng, Rai-Shung Liu
Summary: This study demonstrates gold-catalyzed [3+2]-annulations of alpha-diazo ketones with highly substituted cyclopentadienes, resulting in bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. Enantioselective annulations can also be achieved using chiral forms of gold and phosphoric acid. The mechanistic analysis suggests that cyclopentadienes act as nucleophiles attacking gold carbenes, leading to gold enolates that complex with chiral phosphoric acid to enhance enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xiang Wu, Li-Ping Zhao, Jin-Ming Xie, Yan-Ming Fu, Cheng-Feng Zhu, You-Gui Li
Summary: This study describes a gold-catalyzed cyclization reaction for the synthesis of 3-sulfonamidoquinolines, featuring a rare and highly selective 1,2-N migration. The key alpha-imino gold carbene intermediate is generated through an intramolecular nucleophilic attack of the azide group to the Au-activated triple bonds in a 6-endo-dig manner.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dongxin Zhang, Qihang Cheng, Lvjia Chen, Huiqing Deng, Hu Cai, Qian-Feng Zhang
Summary: Copper triflate-catalyzed annulations of oxindole based spirocyclic donor-acceptor cyclopropanes and ynamides have been developed for the synthesis of biologically important spirocyclopenteneoxindoles. These reactions tolerated a wide scope of substrates and provided the desired products in good to high yields with high diastereoselectivities under mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yongxiang Zheng, Baptiste Moegle, Santanu Ghosh, Anna Perfetto, Davide Luise, Ilaria Ciofini, Laurence Miesch
Summary: A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N-allenamides has been reported, providing a facile and rapid access to terminal N-allenamides with wide functional group compatibility on the nitrogen. This method was successfully applied to the synthesis of fluorine-substituted N-allenamides, which are important building blocks in various fields. DFT calculations provided insights into the mechanism involved in this reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Sakamuri Sarath Babu, A. Anagha Varma, Purushothaman Gopinath
Summary: We report a substrate-controlled cascade cyclization method for constructing functionalized heterocycles using photoredox catalysis under mild conditions. This versatile method has been successfully applied to a wide range of substrates and for the synthesis of functionalized etifoxine drug derivatives.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Souta Misawa, Asaki Miyairi, Yoshihiro Oonishi, Steven P. Nolan, Yoshihiro Sato
Summary: Polarized alkynes such as ynol ethers and ynamides undergo Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reactions with allylic alcohols, proceeding under mild conditions with high regioselectivity. The resulting gamma,delta-unsaturated esters or amides are formed in an atom-economical manner using the [Au(IPr)NTf(2)] catalyst.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Cheng Zhang, Qiaoying Sun, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Summary: In this study, a new strategy is proposed for controlling the selectivity of catalytic reactions by adjusting the electronic and steric properties of metal complexes. The high regioselectivity of the reaction is achieved with the use of an additive, and a novel intramolecular cascade fluorination process is described for the synthesis of aryl fluorides.
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)