Article
Chemistry, Organic
Liu-Liang Mao, An-Xi Zhou, Xian-Hong Zhu, Huanan Peng, Li-Xia Quan, Jie-Ping Wan, Shang-Dong Yang
Summary: We have developed an efficient and facile visible-light-mediated tandem difluoromethylation/cyclization of alkenyl aldehydes using easily accessible and air-stable [Ph3PCF2H]Br-+(-) as the difluoromethylation reagent. Various CF2H-substituted chroman-4-one skeletons and their derivatives are efficiently produced in moderate to good yields with excellent chemoselectivity under mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Ya-Nan Li, Fan Chen, Xing-Guo Zhang, Hai-Yong Tu
Summary: An iodine-mediated radical cyclization reaction of o-vinylaryl isocyanides with disulfides or diselenides has been developed, providing an atom-economic method for the regioselective construction of 2-chalcogenated quinolines with high yields by incorporating both chalcogen atoms of the disulfides or diselenides.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Weiguang Yang, Yu Zhao, Qingxia Bu, Li Li, Baojing Zhou, Zunnan Huang
Summary: A novel synthesis method has been developed for functionalized dihydrooxazines through a tandem reaction under mild conditions. The involvement of N-sulfonyl acylketenimines in [4 + 2] cycloadditions is a notable feature, and the resulting dihydrooxazines can be converted to 2-aminopyridines under basic conditions.
Article
Chemistry, Organic
Kazutoshi Nishimura, Shibo Xu, Yuji Nishii, Koji Hirano
Summary: A metal-free, phosphenium-dication-mediated sequential C-P and C-C bond forming reaction has been developed for the concise synthesis of (di)benzophosphole derivatives from readily available and simple arylalkynes and phosphinic acids. The application of this protocol to multiple cyclization reactions and fully intermolecular three-component coupling-type reactions is also described.
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, Organic
Chunyu Han, Yaowen Liu, Xianhai Tian, Frank Rominger, A. Stephen K. Hashmi
Summary: A dual gold/silver-catalyzed cascade reaction was described for the synthesis of indolizines, yielding compounds with diverse functionalities in good to excellent yield. Furthermore, a gram-scale reaction was efficiently conducted in this study.
Article
Chemistry, Organic
Anirban Bera, Sk Abulkalam Azad, Prasanta Patra, Nayim Sepay, Rathin Jana, Tapas Das, Amit Saha, Shubhankar Samanta
Summary: Here, a weak acid-promoted tandem aza-Michael-aldol strategy has been presented for the synthesis of diversely fused pyrrolo[1,2-a]quinoline. The protocol allows for the construction of both pyrrole and quinoline ring in one pot, forming two C-N bonds and one C-C bond under transition-metal-free conditions. A ketorolac drug analogue and a tricyclic pyrrolo[1,2-a]quinoline fluorophore were successfully synthesized, with the latter being used to detect picric acid via fluorescence quenching.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jieyin He, Liangliang Yang, Xue Zhang, Wendi Xu, Haiyang Wang, Ming Lang, Jian Wang, Shiyong Peng
Summary: This study reports a catalyst-controlled reaction that utilizes gold and iron catalysts to synthesize two series of N-heterocycles, 1,4-diazepanes and 1,4-diazabicyclo[4.3.1]decanes. The reaction proceeds under mild conditions with moderate to high yields. Mechanistic investigations reveal the role of water in the reaction.
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
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
Rebeka Eshagh Saatlo, Jan P. Matiba, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Summary: This paper reports a gold(I)-catalyzed cyclization reaction that directly synthesizes cyclopenta-fused anthracenes (CP-anthracenes) from easily available triene-yne systems with a benzofulvene substructure. These target compounds are of great interest for their potential use as organic materials and the preparation of these compounds is gaining significant importance. The starting materials used in this study are readily available through a three-step synthesis, which further highlights the advantages of this approach. In addition, UV-Vis and fluorescent spectra of the synthesized CP-anthracenes were recorded.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Xinpeng Sang, Yuhao Mo, Shiya Li, Xiaohua Liu, Weidi Cao, Xiaoming Feng
Summary: A bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl-ene reaction was developed, which could produce chiral 5-oxazoylmethyl & alpha;-silyl alcohols with high yield (up to 95%) and enantioselectivity (99% ee) using a broad range of N-propargylamides and acylsilanes under mild conditions. Importantly, this protocol is applicable for the late-stage modification of several bioactive molecules.
Article
Chemistry, Organic
Chun-Yong Jiang, Hui Xie, Zhuo-Jun Huang, Jing-Yi Liang, Yan-Xia Huang, Qiu-Ping Liang, Jun-Yi Zeng, Binhua Zhou, Shang-Shi Zhang, Bing Shu
Summary: An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance, while also presenting a possible mechanistic proposal.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Christoph Etling, Giada Tedesco, Markus Kalesse
Summary: This study investigated the different reactivity of trienones under Lewis and Bronsted acids catalysis, resulting in novel Nazarov cyclization tandem reactions terminating oxyallyl cations by ene-type reactions. The bicyclic spiro compounds produced were shown to be useful intermediates for further functionalization. Furthermore, the tandem Nazarov/ene cyclization was found to be preferred over a Nazarov/[3+2] tandem reaction for all substrates, regardless of chain length.
CHEMISTRY-A EUROPEAN JOURNAL
(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)