Article
Chemistry, Multidisciplinary
Ji-Wei Sang, Ming-Sheng Xie, Man-Man Wang, Gui-Rong Qu, Hai-Ming Guo
Summary: In this study, the first chemoselective C-C bond cleavage ring-opening reaction of D-A oxiranes with N-heteroaromatics was achieved using Y(OTf)(3) as the catalyst. Various N-heteroaromatics reacted well with different D-A oxiranes, providing acyclic nucleoside analogues with high yields and regioselectivity. Additionally, a Ganciclovir analogue could be obtained through simple transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yasunori Toda, Kayo Sato, Kensuke Sato, Kazuma Nagasaki, Hirotaka Nakajima, Ayaka Kikuchi, Kimiya Sukegawa, Hiroyuki Suga
Summary: This paper reports on the chiral binaphthyldiimine-Ni(II)-catalyzed asymmetric 1,3-dipolar cycloaddition reactions between acyclic carbonyl ylides generated from donor-acceptor oxiranes and aldehydes. Both aromatic and aliphatic aldehydes can be used as dipolarophiles, providing cis-1,3-dioxolanes with high diastereo- and enantioselectivities. Mechanistic studies suggest that a monomeric chiral Ni(II) complex acts as the active species for the cycloaddition, and the high levels of asymmetric induction can be explained by a concerted-asynchronous endo Si-face approach of the aldehyde.
Article
Chemistry, Organic
Meng-Cheng Zhang, Dong-Chao Wang, Hai-Ming Guo, Gui-Rong Qu, Hai-Ting Wang
Summary: A new Ni(II)/bisoxazoline-catalyzed asymmetric dearomative [3+2] cycloaddition of substituted purines with donor-acceptor oxiranes was developed. This reaction proceeds via highly chemoselective C-C bond cleavage of the oxiranes, resulting in the formation of chiral purino[3,2-c]oxazole compounds. The reactivity of the substrate is influenced by the electronic effects of the purine ring. The general applicability of this method was demonstrated through gram-scale synthesis, diverse transformations of the product, and the promising biological activities of selected derivatives.
Article
Chemistry, Organic
Miao-Dong Su, Hai-Ping Liu, Zhong-Zhong Cao, Yufeng Liu, Hui Li, Zhi-Wen Nie, Tong-Lin Yang, Wei-Ping Luo, Qiang Liu, Can-Cheng Guo
Summary: In this study, annulation to pyridines using two C=C bond participation was conducted with DMF as the Ni and C4 synthons, providing a convenient and efficient method for the synthesis of symmetric and unsymmetric diaryl-substituted pyridines in useful yields. Through relevant literature and experimental results, a possible mechanism was proposed to explain how DMF can serve as both N1 and C4 sources in this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Prabhat K. Maharana, Tanumay Sarkar, Subhradeep Kar, Siddhartha K. Purkayastha, Ankur K. Guha, Tharmalingam Punniyamurthy
Summary: Stereospecific C-N and C-O bond formation of oxiranes with diaziridines has been achieved using a bimetallic catalyst at room temperature, resulting in the production of tetrahydro-[1,3,4]-oxadiazines. Optically active oxiranes can be coupled with high optical purities (>96% ee). The practical significance of this method lies in its stereoselectivity, tolerance for various functional groups, mechanistic studies using DFT, and potential application in natural product modification.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Thomas De Dios Miguel, Nam Duc Vu, Marc Lemaire, Nicolas Duguet
Summary: The ring-opening of epoxidized methyl oleate by aqueous H2O2 using tungsten and molybdenum catalysts resulted in the formation of fatty beta-hydroxy hydroperoxides with high selectivity. The optimized conditions allowed for the synthesis of these compounds with isolated yields of 30-80%. Thermal cleavage of these hydroperoxides in flow conditions showed high selectivity towards aldehyde formation with limited byproducts. Overall, the process is efficient and environmentally friendly, generating water as the only byproduct.
Article
Chemistry, Organic
Anna Lo, David A. Gutierrez, Garrett Toth-Williams, James C. Fettinger, Jared T. Shaw
Summary: Lewis acid mediated allylations of beta-alkoxy N-tosyl imines using allyltrimethylsilane led to the formation of anti-selective 3-alkoxy homoallylic N-tosyl amines. Two methods of Cu(OTf)(2)-mediated allylations were reported, showing that diastereoselectivity can be achieved through the 1,3 acyclic stereocontrol of beta-chiral aldimines. The observed selectivity trends and computational evidence suggest that selectivity arises through the formation of a six-membered ring chelate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Yui Kawamura, Daisuke Hotta, Arihiro Kanazawa, Sadahito Aoshima
Summary: The types and numbers of alkyl substituents were found to affect the reactivity of oxiranes in cationic copolymerization with alkyl vinyl ethers. Oxiranes with bulkier substituents showed lower reactivity, while oxiranes with fused ring structures exhibited higher reactivities. These results provide a systematic understanding of the polymerizability of oxiranes.
Article
Chemistry, Multidisciplinary
Ziwei Zhao, Zhanrong Zhang, Qinglei Meng, Bingfeng Chen, Jinliang Song, Huizhen Liu, Buxing Han
Summary: Effectively cleaving and functionalizing C(OH)-C bonds is crucial for producing valuable chemicals from renewable biomass resources. The inert nature of C(OH)-C bonds and various side reactions associated with hydroxyl groups hinder their oxidative cleavage efficiency and selectivity. Converting secondary alcohols to aldehydes is particularly challenging due to the tendency of over-oxidation. Noble-metal catalysts are necessary to achieve satisfactory aldehyde yields.
Article
Chemistry, Multidisciplinary
Kuo Zhao, Gesa Seidler, Robert R. Knowles
Summary: A method for the isomerization of acyclic allylic alcohols into beta-functionalized ketones via 1,3-alkyl transposition is described. The reaction proceeds through light-driven proton-coupled electron transfer (PCET) activation and C-C beta-scission, leading to the formation of beta-functionalized ketone products. Insights from mechanistic studies have led to an improved reaction protocol for challenging substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Magesh Sampath, Sembian Ruso Jayaraman, Vishnuvardhan Reddy Eda, Rajendar Potham, Rajeev Rehani Budhdev, Saikat Sen, Rakeshwar Bandichhor, Srinivas Oruganti
Summary: An efficient and elegant enantioselective synthesis of the key chiral pyrrolidine fragment for Upadacitinib (ABT-494) was described using Oppolzer's chiral sultam-directed asymmetric 1,3 dipolar cycloaddition. The method provided the desired level of diastereoselectivity and enantioselectivity in the construction of the 3,4-syn substituted pyrrolidine moiety.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Chuan-Ming Hong, Si-Qi Xiong, Xue Zhang, Kai-Xian Ma, Qing-Hua Li, Tang-Lin Liu
Summary: This paper discloses a silver-catalyzed 1,3-aza-benzyl migration of allyl alcohols by utilizing chelation-assisted selective cleavage of an unstrained C(sp3)-C(sp3) bond. This approach provides an available, efficient, high atom-economic, and environmentally benign procedure, leading to alkylation products with broad substrate scopes and excellent yields. The migration proceeds via a one-pot, two-step process involving a free-state alkyl metal species.
Article
Chemistry, Multidisciplinary
Shiqi Jia, Yu Chang, Yuhong Tian, Hui Mao, Wenling Qin, Pengfei Wang, Hailong Yan
Summary: An organocatalytic approach using VQM intermediates was employed to introduce various alcohols into the carbonyl of alpha,beta-unsaturated ketones, followed by dearomatization to yield stereo-defined cyclic ethers via a cascade process. This strategy provides efficient access to the unexplored chiral cyclic ether chemospace.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Lina Ma, Hua Zhou, Xianggui Kong, Zhenhua Li, Haohong Duan
Summary: The study presents an efficient electrocatalytic strategy for cleaving C-alpha-C-beta bonds in lignin model compounds at room temperature using platinum as the anode and tert-butyl hydroperoxides as the oxidants, resulting in high yields of aromatic aldehydes and phenols. This electrocatalytic strategy is highly selective and can transform a wide range of lignin models and polymers into desired aromatic aldehydes. Mechanistic studies suggest that the reaction proceeds via a C-beta radical process involving a peroxide intermediate, showing potential for using renewable electricity to selectively break C-alpha-C-beta bonds and transform lignin into valuable chemicals under ambient conditions.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Chen-Xi Ye, Xiang Shen, Shuming Chen, Eric Meggers
Summary: In this study, a protocol for the synthesis of α-amino acids was reported, which is based on a stereocontrolled 1,3-nitrogen shift. This method uses abundant and easily accessible carboxylic acids as starting materials and a regio- and enantioselective ruthenium- or iron-catalysed C(sp(3))-H amination. It provides a rapid access to optically active α-amino acids with various side chains.
Article
Chemistry, Medicinal
Christine Brotherton-Pleiss, Peibin Yue, Yinsong Zhu, Kayo Nakamura, Weiliang Chen, Wenzhen Fu, Casie Kubota, Jasmine Chen, Felix Alonso-Valenteen, Simoun Mikhael, Lali Medina-Kauwe, Marcus A. Tius, Francisco Lopez-Tapia, James Turkson
Summary: The study optimized proline-based STAT3 inhibitors into a new series of azetidine-2-carboxamide analogues with sub-micromolar potencies, demonstrating potential therapeutic effects on breast cancer cells.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Qian Yang, Guanglong Pan, Jie Wei, Wentao Wang, Yurong Tang, Yunfei Cai
Summary: By modifying the structure of carbon nitride, a heterogeneous photocatalytic system for both decarboxylative addition and reductive dimerization has been developed with remarkable catalytic activity. The system offers advantages such as lower catalyst loading, enhanced optical absorption, improved electron-hole separation, good recyclability, broad substrate scope, and easy scale-up in continuous flow for valued target synthesis.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Guanglong Pan, Qian Yang, Wentao Wang, Yurong Tang, Yunfei Cai
Summary: A visible light-mediated heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile was established using CN-K as a recyclable semiconductor photocatalyst. This method allows for the efficient construction of a wide array of nitrogenous heterocyclic compounds with structural diversity, including indolines, oxindoles, isoquinolinones, and isoquinolinediones, by employing NHPI ester as a radical initiator.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yonghai Hui, Yongfei Zhang, Jianpeng Li, Biao Yu, Bing Han, Yun Wang, Jialiang Xia, Shiqi Zhang, Weiliang Chen
Summary: A heterogeneous catalytic system using unfunctional mesoporous material MCM-41 was developed for one-pot synthesis of spiro[indoline-3,2'-pyrrolidin]-ones, achieving good yields of up to 95% in water/ethanol = 2/1 solvent. The catalyst could be easily recovered and reused at least 10 times without loss in activity, highlighting its reusability, operational simplicity, and eco-friendliness.
Article
Chemistry, Organic
Lei Xu, Hongxiang Li, Liuzhuang Xing, Qian Yang, Yurong Tang, Yunfei Cai
Summary: A novel aza-Piancatelli rearrangement triggered cascade reaction was developed, allowing for rapid construction of diverse cyclopenta[b]pyrrolidinone derivatives. The unprecedented and highly efficient bicyclic gamma-lactam product formation is originated from an unusual retro-aza-Piancatelli rearrangement of the major cis-fused multifunctionalized cyclopentenone to the minor trans-fused one followed by a lactamization reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Sishi Zhong, Lei Xu, Yunfei Cai
Summary: The Piancatelli reaction is a significant organic synthesis reaction, which can construct diversified functionalized cyclopentenones and polycyclic cyclopentanones. In addition, there have been developments in chiral catalytic reactions in this field.
SYNTHESIS-STUTTGART
(2022)
Article
Oncology
Peibin Yue, Yinsong Zhu, Christine Brotherton-Pleiss, Wenzhen Fu, Nagendra Verma, Jasmine Chen, Kayo Nakamura, Weiliang Chen, Yue Chen, Felix Alonso-Valenteen, Simoun Mikhael, Lali Medina-Kauwe, Kathleen M. Kershaw, Maria Celeridad, Songqin Pan, Allison S. Limpert, Douglas J. Sheffler, Stephen L. Shiao, Marcus A. Tius, Francisco Lopez-Tapia, James Turkson
Summary: In this study, potent azetidine-based, selective, irreversible Stat3 inhibitors were identified that inhibit the growth of triple-negative breast cancer. These compounds amplify the Stat3-inhibitory activity and selectively bind to Stat3, leading to the inhibition of constitutive and ligand-induced Stat3 signaling. The inhibitors showed no effect on other proteins or cells without aberrantly-active Stat3.
Article
Chemistry, Organic
Hongxiang Li, Qian Yang, Lei Xu, Jie Wei, Yurong Tang, Yunfei Cai
Summary: In this study, an asymmetric three-component rearrangement of alkenylfurans with various sulfonyl chlorides and anilines was developed via copper(I) and chiral vanadium cooperative catalysis, providing a facile access to a broad spectrum of sulfonylfunctionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities.
Article
Chemistry, Organic
Jiaming Zou, Lei Xu, Yurong Tang, Wentao Wang, Yunfei Cai
Summary: The asymmetric synthesis of bridged tetrahydrobenzo[b]azepine and oxepine derivatives has been achieved through chiral Bri nsted acid catalyzed asymmetric aza-Piancatelli rearrangement/Michael addition sequence. The reaction proceeds under mild reaction conditions to afford the final bridged cyclic products in good yields with excellent enantio- and diastereoselectivities.
Article
Chemistry, Organic
Jie Wei, Yurong Tang, Qian Yang, Hongxiang Li, Dongxian He, Yunfei Cai
Summary: An enantioselective three-component rearrangement of alkenylfurans has been developed by merging photoredox catalysis with chiral Brønsted acid catalysis. This protocol provides expedient access to a broad spectrum of ketoalkyl-functionalized 4-aminocyclopentenones in high yields with excellent enantio- and diastereoselectivities. Diverse functional groups can be introduced via facile product derivations.
Article
Chemistry, Organic
Xiao Dan, Qian Yang, Liuzhuang Xing, Yurong Tang, Wentao Wang, Yunfei Cai
Summary: A fully heterogeneous metallaphotocatalytic C-C cross-coupling of aryl/vinyl halides with alkyl/allyl trifluoroborates has been developed using an integrated bipyridyl-Ni-(II)-carbon nitride as a stable and recyclable bifunctional catalyst. This visible-light-mediated heterogeneous protocol enables the sustainable synthesis of diverse valuable diarylmethanes and allylarenes in high efficiency.
Article
Multidisciplinary Sciences
Liuzhuang Xing, Qian Yang, Chen Zhu, Yilian Bai, Yurong Tang, Magnus Rueping, Yunfei Cai
Summary: In this study, the authors successfully incorporated privileged homogeneous bipyridyl-based Ni-catalysts into highly ordered and crystalline potassium poly(heptazine imide) (K-PHI), achieving the development goal of heterogeneous metallaphotocatalysis. The LnNi-PHI catalysts exhibit superior chemical stability and recyclability in C-P, C-S, C-O and C-N cross-coupling reactions.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Yilian Bai, Qian Yang, Yurong Tang, Xiao Dan, Wentao Wang, Yunfei Cai
Summary: In this study, a recyclable catalyst, Cu-doped carbon nitride (Cu-CN), was developed as a Cu-photo dual catalytic system. The heterogeneous CN-Cu catalyst can be used for direct alpha-alkynylation of tertiary amines using air as an oxidant, resulting in high yields of diverse propargylamines. The endogenous proximity and synergistic effect between Cu and the photocatalytic center in CN-Cu significantly enhance the Cu-photo dual catalytic activity, improving reaction efficiency and selectivity. Remarkably, this heterogeneous catalyst exhibits high chemical stability and can be recycled at least five times without loss of activity.
Article
Chemistry, Multidisciplinary
Yonghai Hui, Jianpeng Li, Biao Yu, Xuejiang Xing, Tianming Gao, Xiaoyan Qian, Yongfei Zhang, Weiliang Chen
Summary: In this study, efficient and recoverable amine-functionalized mesoporous materials were used for the synthesis of sulfur/dinitrogen-containing heterocycles in water. The desired thiazine heterocyclic compounds were obtained in high yields and the catalyst showed good recyclability. The study also provided insights into the possible mechanism of the reaction.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Fan Du, Xiaojie Zhou, Yilian Bai, Qing Tang, Yunfei Cai, Yurong Tang
Summary: Three metal-containing species (Mn, Ce, Eu) were constructed in carbon nitride (CN) nanocomposites through surface modification strategy. The nanocomposites showed outstanding photo-responsive oxidase-mimicking activity and colorimetric sensing properties.
NEW JOURNAL OF CHEMISTRY
(2022)
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)
