Article
Chemistry, Organic
Sudip Shit, Bipin Kumar Behera, Subhamoy Biswas, Anil K. K. Saikia
Summary: A metal-free Lewis acid-initiated protocol has been developed for the synthesis of highly substituted 3-(dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines. The reaction involves the formation of dihydrofuranylidene carbocation followed by intramolecular cyclization, leading to the desired products in moderate to good yields. The methodology can also be extended to the synthesis of 3-(dihydro-2H-pyran-3(4H)-ylidene)-isobenzofuran-1(3H)-imines, and furanylidene isobenzofuranones can be obtained in excellent yields through post synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhen Liu, Mitch Mathiew, Jichao Chen, Xiangdong Yu, Dandan Shang, Javey Khiapeng Tan, Philip Wai Hong Chan, Weidong Rao
Summary: A synthetic method for the efficient preparation of a structurally diverse range of spirocyclic pyrrolidines and piperidines has been developed. The method relies on the gold(i)-catalyzed spirocyclization of 1-ene-4,9- and 3-ene-1,7-diyne esters, and allows for the synthesis of spirocyclic cyclopentanes, furans, pyrrolidines and piperidines. The method also shows potential for late-stage modification of complex natural products and drug molecules under mild reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yifan Wang, Yuanyuan Ping, Wangqing Kong
Summary: A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B 2 Pin 2 and alkenetethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Jhansi Rani Morla, Dastagiri Reddy Nareddula
Summary: This study reports the synthesis of dihydroisoquinolinone-4-methylboronic esters from N-allylcarboxamides and B-2(Pin)(2)via a domino Heck/borylation approach. A quinoxaline-based NHC-palladacycle [Pd(C boolean AND C:)PPh3Cl], which has been structurally characterized, is used as a catalyst. The scope of the substrate with a wide range of substituents is explored. In addition to the synthesis of the title compounds, a few examples of methylboronic esters of indoline and benzofuran motifs have also been prepared using the same protocol.
Article
Chemistry, Organic
Yu-Qing Li, Guang Chen, Shi-Liang Shi
Summary: This Ni-catalyzed three-component coupling reaction provides a general synthetic approach to 1,4-disubstituted homoallylic alcohols, which were previously difficult to access. The reaction is regioselective, trans-selective, and can tolerate highly base-sensitive functional groups under neutral conditions.
Article
Chemistry, Multidisciplinary
Santosh J. Gharpure, Dipak J. Fartade, Krishna S. Gupta, Raj K. Patel
Summary: The TMSOTf-mediated reaction of alkynyl vinylogous carbonates unexpectedly generates 1,4-oxazepine and dihydropyran dienes through the transposition of an ethyl acrylate moiety via an intramolecular cascade Prins-type cyclization/retro-oxa-Michael reaction/cycloisomerisation. This atom-economical protocol selectively produces a specific E double bond geometry, and the dihydropyran dienes can be further transformed into polycyclic heterocycles using the Heck reaction.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Hongbo Qi, Kaiming Han, Shufeng Chen
Summary: This novel palladium-catalyzed aryl-furanylation of alkenes provides a straightforward route to various benzofuran-containing 3,3-disubstituted oxindole derivatives bearing a quarternary carbon center. In a single chemical operation, one C(sp(2))-O bond, two C(sp(2))C(sp(3)) bonds, an oxindole, and a furan ring are formed in the cascade process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu. Sukhorukov
Summary: In this work, the classical approach to aldol synthesis using isoxazoline was revisited. A [4 + 1] annulation reaction was used to construct the isoxazoline ring bearing an N-oxide moiety to avoid regioselectivity issues. The resulting alpha'-acyloxy-substituted aldols were obtained with good yields and as single diastereomers in most cases. The synthetic use of these aldols was demonstrated by their transformation into diastereomerically pure triols and a structurally related tetrahydrofuran derivative.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Marine Pinaud, Eric Huet, Marc Presset, Erwan Le Gall
Summary: A straightforward and modular method for the synthesis of substituted spirocyclic tetrahydrofurans is described. The strategy involves a reductive cobalt-catalyzed three-component reaction and an intramolecular iodoetherification reaction, allowing for the preparation of diverse spirocyclic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chinnabattigalla Sreenivasulu, Gedu Satyanarayana
Summary: The development of synthetic strategies for stereo- and regioselective synthesis is crucial in the pharmaceutical industry. This work demonstrates a novel palladium-catalyzed synthesis of (E)/(Z)-1,1-disubstituted-3-(1-arylalkylidene)-1,3-dihydroisobenzofurans. The study also reveals the formation of Z-isomer as a substantial isomer at lower temperature conditions, while the E-isomer is predominant under slightly more vigorous conditions. Additionally, the observation of double isomerization from Z- to E-isomer in the NMR tube itself at room temperature is significant.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Akihiro Koga, Maki Matsuda, Rin Tanaka, Minami Endo, Yasunori Yamada, Takeshi Hanamoto
Summary: In this study, various nitrogen nucleophiles were easily added to in situ-generated 1-(trifluoromethyl)-2-(phenylthio)ethyne to afford the corresponding trifluoromethyl enamines in good-to-high yields and with high regio- and stereocontrol under very mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Tomasz J. Idzik, Zofia M. Myk, Lukasz Struk, Magdalena Peruzynska, Gabriela Maciejewska, Marek Drozdzik, Jacek G. Sosnicki
Summary: A novel method for the arylation of enelactams using TIPSOTf as the catalyst, with high yield up to 99%, has been proposed. The reaction mechanism and intermediates were identified using multinuclear NMR spectroscopy, and the method showed potential for synthesizing polycyclic systems. The inhibition of melanoma cell proliferation by some benzoquinolizidine derivatives was also demonstrated.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Siyang Xing, Chenyu Wang, Tingxuan Gao, Yuhan Wang, Hongzheng Wang, Hanfei Wang, Kui Wang, Bolin Zhu
Summary: A stepwise cyclization method has been developed for the synthesis of 4-spiroannulated tetrahydroisoquinoline compounds, which involves sequential ring opening of aziridines and Pictet-Spengler reaction. This strategy exhibits high bonding and cyclization efficiency, broad substrate scope, mild reaction conditions, and good generality of the ring size in the product.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Weicheng Zhang
Summary: The Heck macrocyclization reaction is an extension of the award-winning Mizoroki-Heck reaction, forming macrocycles by linking two coupling partners. This method has become a viable option for synthesizing diverse macrocycles and is significant in natural product synthesis.
NATURAL PRODUCT REPORTS
(2021)
Article
Chemistry, Organic
Jiaheng Li, Wei Ma, Wenbo Ming, Cong Xu, Na Wei, Mang Wang
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Xiaoning Song, Jian Chang, Dongsheng Zhu, Jiaheng Li, Cong Xu, Qun Liu, Mang Wang
Article
Chemistry, Organic
Jiaheng Li, Cong Xu, Na Wei, Mang Wang
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Xiaoning Song, Cong Xu, Dongxu Du, Ziming Zhao, Dongsheng Zhu, Mang Wang
Article
Chemistry, Organic
Jian Chang, Cong Xu, Jie Gao, Fengyun Gao, Dongsheng Zhu, Mang Wang
Article
Chemistry, Organic
Xiaoning Song, Cong Xu, Mang Wang
TETRAHEDRON LETTERS
(2017)
Article
Chemistry, Organic
Cong Xu, Xiaoning Song, Jia Guo, Sibao Chen, Jie Gao, Jing Jiang, Fengyun Gao, Yuxin Li, Mang Wang
Review
Chemistry, Applied
Cong Xu, Mang Wang, Qun Liu
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Cong Xu, Wanqiao Huang, Ruzhong Zhang, Chi Gao, Yuxin Li, Mang Wang
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Cong Xu, Na Wei, Dongsheng Zhu, Mang Wang
Article
Chemistry, Organic
Wanqiao Huang, Cong Xu, Jianxin Yu, Mang Wang
Summary: An effective method for the aminotrifluoromethylation of alkenes was developed by using PhICF3Cl and ZnI2 as catalysts. The mechanism studies showed that the reaction involves an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ru Zhong Zhang, Ru Xue Zhang, Shuang Wang, Cong Xu, Wei Guan, Mang Wang
Summary: In this study, an alternative and scalable cyclization strategy based on NCF3-containing synthons was used to construct N-CF3 azoles. This approach allows for the divergent synthesis of N-trifluoromethylated tetrazoles, imidazoles, and 1,2,3-triazoles using various dipoles. The introduction of CF3 onto the nitrogen of heterocycles provides a direct route to such motifs, overcoming the limitations of traditional methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ru Zhong Zhang, Wanqiao Huang, Ru Xue Zhang, Cong Xu, Mang Wang
Summary: An efficient methodology for synthesizing a wide range of N-CF3 imidic acid derivatives is presented. The method involves the generation of N-CF3 nitrilium ions from nitriles using PhICF3Cl under catalysis with DMAP, followed by the capture of N-, O-, or S-centered nucleophiles to produce diverse N-CF3 amidines, imidates, and thioimidates. This method provides a platform for preparing N-CF3 compounds with potential applications.
Article
Chemistry, Organic
Jia Guo, Cong Xu, Ling Wang, Wanqiao Huang, Mang Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Jia Guo, Cong Xu, Xiaowei Liu, Mang Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
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)
