Article
Chemistry, Organic
Atsushi Kimishima, Hiroki Kato, Keijin Nakaguro, Masayoshi Arai
Summary: A method for synthesizing C3a acetoxy hexahydropyrrolo[2,3-b]indole derivatives has been developed using a PhI(OAc)(2)/(Bu4NI)-Bu-n mediated tandem iodocyclization/acetoxylation. This newly developed synthesis approach allows for the efficient assembly of various C3a acetoxylated tetrahydropyrrole-, tetrahydrofuran-, and lactone-fused indolines under mild reaction conditions, enabling the asymmetric synthesis of (-)-protubonine B.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Masaki Fujie, Kyohei Mizufune, Yoshihiro Nishimoto, Makoto Yasuda
Summary: Proximal aryl C-H sulfonyloxylation and acetoxylation on 2-iodo-1,1-biphenyl structures have been achieved using λ3-iodane as a catalyst. The key step in this reaction involves intramolecular electron transfer between cationic I(III) and proximal 2-Ar groups in 2-arylphenyl-lambda 3-iodanes, leading to the generation of an iodanyl radical intermediate with a radical cationic Ar moiety. This intermediate then undergoes nucleophilic addition of acetate or sulfonate. The proposed mechanism is supported by electron spin resonance experiments. A 2-benzyl-iodobenzene structure is also compatible with this reaction system.
Article
Chemistry, Organic
Baibin Li, Jingwen Yuan, Xuebei Ye, Rui Zhang, Jiacheng Li, Yu Wang, Jiana Hu, Dewen Dong
Summary: A novel method for the synthesis of polysubstituted oxazol-2(3H)-ones has been developed, featuring readily available starting materials, mild reaction conditions, high chemoselectivity, good functional group tolerance, and a metal-free oxidation process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Baibin Li, Jingwen Yuan, Xuebei Ye, Rui Zhang, Jiacheng Li, Yu Wang, Jiana Hu, Dewen Dong
Summary: This efficient method using PIFA-mediated tandem reaction can synthesize polysubstituted oxazol-2(3H)-ones, with advantages of readily available starting materials, mild conditions, simple execution, high selectivity, and metal-free oxidation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Quan-Bing Wang, Shi Tang, Ying-Jie Wang, Yue Yuan, Tieqiao Chen, Ai-Qun Jia
Summary: The PIDA mediated intramolecular oxidative C-N coupling and subsequent detosylative aromatization allowed for the synthesis of valuable indolo[2,3-b]quinoline derivatives, providing an efficient method for their preparation.
Review
Chemistry, Organic
Irina A. Mironova, Stefan F. Kirsch, Viktor V. Zhdankin, Akira Yoshimura, Mekhman S. Yusubov
Summary: This review summarizes recent approaches to the direct synthesis of organic azides using hypervalent iodine reagents. The first part discusses the use of unstable azidoiodinanes generated in situ, while the second part focuses on the application of stable azidobenziodoxoles as azidating reagents. The use of azidobenziodoxoles allows for selective direct azidation of specific bonds under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Mary Anne Maverick, Mathieu Noel, Jean-Jacques Vasseur, Carine Baraguey, Francoise Debart, Michael Smietana
Summary: It has been observed that 2',3'-O-isopropylidene analogue of N4-acetylcytidine undergoes an unprecedented oxidative cyclization in the presence of hypervalent iodine(III) in water, resulting in a mixture of C5-substituted O6,5'-cyclo-5,6-dihydrouridines. These cyclouridines can be opened under basic conditions and further synthesized into an important post-transcriptional modification of bacterial tRNA.
Article
Chemistry, Applied
Yuna Nishiguchi, Katsuhiko Moriyama
Summary: A new synthetic method was developed with the use of aniline-type hypervalent iodine(III) for direct cyclizations, resulting in high yields of the corresponding products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Lingchao Cai, Liangliang Song
Summary: This study reports a hypervalent iodine-mediated bicyclization method for the synthesis of polyheterocycles. The synthesized tetracyclic isoquinolones demonstrate good fluorescent properties and exhibit promising antifungal activity against crop and forest pathogenic fungi.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Mirdyul Das, Arantxa Rodriguez, Pui Kin Tony Lo, Wesley J. Moran
Summary: This study presents the preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates, allowing for a versatile range of substrates to be converted into substituted oxazolidinones ready for further transformations. Derivatization of the products at both ends is demonstrated in addition to a preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Chunyu Han, Xianhai Tian, Lina Song, Yaowen Liu, A. Stephen K. Hashmi
Summary: A gold-catalysed cascade reaction for the synthesis of tetra-substituted furans from acceptor-substituted carbonyl compounds using hypervalent iodine(iii) reagents was described. This method involves two Au(i)/Au(iii) catalytic cycles and allows for gram-scale synthesis, with the synthesized furan product easily transformed into other related compounds. The reaction offers distinct advantages over previous methods and can tolerate a wide range of functionalities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Prafull A. Jagtap, Manjunath S. Lokolkar, Bhalchandra M. Bhanage
Summary: A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds was developed. The reaction involves copper-mediated tandem hydroamination followed by C-H annulation of unprotected anilines with internal alkynes. The reaction proceeds well with Cu(OAc)(2)& BULL;H2O and trifluoroacetic acid (TFA), providing various substituted indole derivatives in moderate to good yields. The process is compatible with primary and secondary anilines as well as aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, demonstrating the cost-effectiveness and environmentally benign nature of the protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Artem V. Semenov, Sergey V. Baykov, Natalia S. Soldatova, Kirill K. Geyl, Daniil M. Ivanov, Antonio Frontera, Vadim P. Boyarskiy, Pavel S. Postnikov, Vadim Yu. Kukushkin
Summary: Five new copper(I) complexes were generated and isolated as a solid via a three-component reaction. These complexes consist of dibenzohalolium cation and 1,2,4-oxadiazolate anion, with simultaneous linkage between the O,O atoms of the anion and the halogen atom. The strong three-center halogen bonding between the oxadiazolate moieties and the dibenzohalolium cation was identified as the main force in stabilizing the copper(I) complexes.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Wu, Na Liao, Qi Wei, Jiaying Huang, Qi Huang, Yungui Peng
Summary: An efficient asymmetric tandem reaction catalyzed by chiral silver imidodiphosphate has been developed for the synthesis of chiral 1,2-dihydroisoquinoline analogues with a tertiary stereocenter at the C1 position. The products can be further elaborated into beta-aminophosphonates or PARP1-inhibitor analogues with high yields and ee values.
Article
Chemistry, Organic
Nicholas R. Lauta, Ryan E. Williams, David T. Smith, Vlad K. Kumirov, Jon T. Njardarson
Summary: A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported, where lead(IV) carboxylates are used to achieve tandem C-N and C-O bond formation at room temperature. Mechanistic and kinetic studies suggest a process involving Wessely dearomatization, cyclization, and rearomatization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
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)