Article
Chemistry, Organic
Ke Li, Zhenjie Gan, Er-Qing Li, Zheng Duan
Summary: A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Article
Chemistry, Multidisciplinary
Xiaohu Li, You Huang
Summary: A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction has been developed for the synthesis of chromeno[4,3-b]pyrrole derivatives. This method provides good yield, excellent chemoselectivity and diastereoselectivity under mild conditions, resulting in compounds containing three contiguous stereogenic centers.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Sachin Chauhan, Shubham Debnath, K. C. Kumara Swamy
Summary: This study reports the Lewis base dependent (3 + 3) annulation of delta-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with delta-acetoxy allenoates via 6-exo-dig cyclization at room temperature (25 degrees C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between N-Boc-oxindole and delta-acetoxy allenoates goes through 6-endo-dig cyclization, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Qiqi Hao, Nan He, Yi Wang, Xiaoyan Yang, Yonghuan Wang, Yanyan Zhu, Lingbo Qu
Summary: The [4 + 2] annulation of allenoates with thiazolone-derived alkenes catalyzed by phosphine was studied using density functional theory. The C-C bond formation is identified as the rate-determining and stereoselectivity-determining step. Catalyst Cat1 favors the formation of R-configured product with high enantioselectivity, while Cat2 does not exhibit enantioselectivity.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ting-Ting Yang, Congcong Wang, Shi-Jun Li, Min Zhang, Donghui Wei, Yu Lan
Summary: The density functional theory calculations provided insights into the mechanisms and selectivity origins of phosphine-catalyzed [2+3] and [2+4] annulations. The results indicated a preference for allenoate as a C3 synthon under phosphine catalysis, with the catalytic cycle involving eight key processes. Additionally, non-covalent interactions were found to significantly contribute to the stability of the transition state, influencing the chemo- and stereo-selectivities of the reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: In this study, a modular approach was used to synthesize a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization. DDQ was utilized for the first time to selectively synthesize the pyrrole units from cyclopropyl pyridines. The regioselective oxidation of the benzylic position by DDQ enabled the access to one regioisomer out of two possible ones. Additionally, homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ was discovered for the first time.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Fuhao Zhang, Xuan Dai, Lei Dai, Wenrui Zheng, Wai-Lun Chan, Xiaodong Tang, Xumu Zhang, Yixin Lu
Summary: A phosphine-catalyzed highly enantioselective and diastereoselective (3+2) annulation reaction has been developed, allowing convenient access to a range of highly functionalized chiral pyrrolidines. This method utilizes vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation, offering new opportunities for the application of cyclopropanes substrates in phosphine-catalyzed organic transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shabbir Ahmed Khan, A. Sanjeeva Kumar, K. C. Kumara Swamy
Summary: DBU-catalyzed spiro-annulation and ring expansion/dominoreaction of delta-acetoxy allenoates with cycl-2-ene-N-sulfonyl hydrazides led to ring-expanded products. On the other hand, cycl-3-ene/ane-N-sulfonyl hydrazones under similar conditions gave pyrazolecores. The key intermediates of spirocyclic and dienyl-amine were isolated and characterized. An extension to (R)-(-)-carvone-derived sulfonyl hydrazide also resulted in ring expansion and formation of pyrazoloazepine.
Article
Chemistry, Organic
Wen-Qing Zhu, Zi-Wei Zhang, Wen-Yong Han, Yu-Chen Fang, Ping Yang, Lin-Qiang Li, Yong-Zheng Chen
Summary: A novel palladium-catalyzed three-component reaction has been developed, which utilizes three different types of compounds to produce a range of new compounds in moderate to good yields. Significantly, aziridine was used as a vinylidene unit for the first time in the products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Palani Manikandan, Rudrasenan Agneswaran, Vinayagam Pavunkumar, Arasambattu K. Mohanakrishnan
Summary: Heteroarylmethylenephosphorus ylides can react with alkynediones and alkynediesters to yield various organic compounds.
Article
Chemistry, Organic
Junfeng Fu, Ingrid Rakielle Tsapy Takia, Peng Chen, Wei Liu, Chengjun Jiang, Weijun Yao, Xiaofei Zeng, Yongjiang Wang, Xiaoyu Han
Summary: The phosphine-mediated tandem [3 + 2] cyclization/intramolecular Wittig reaction of 3-aroylcoumarin with alkynone allows the synthesis of 2-chromanone-fused bicyclo[3.2.0]heptenones in moderate to high yields with remarkably high regio- and diastereoselectivities under mild reaction conditions, providing an extremely simple, economical, and straightforward synthetic method for constructing complex cyclic building blocks with potential biological applications.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Yuxin Ding, Ruiqin Zhang, Renchao Ma, Yongmin Ma
Summary: An iodine-catalyzed double [4+2] oxidative annulation of ketones and diamines is reported, leading to the synthesis of substituted dimeric pyrazines under metal-free conditions through a multi-pathway coupled domino strategy. During this process, one C-C and four C-N bonds are formed from two ketones and two diamines.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Pei-Pei Xu, Jun-Yi Liao, Jia-Jie Zhang, Wei-Min Shi, Cui Liang, Gui-Fa Su, Dong-Liang Mo
Summary: Various N-vinylindoles and N-vinylpyrroles were synthesized in moderate to good yields through nickel(II)-catalyzed [3 + 2] cycloaddition. A rational mechanism for the formation of N-vinylindoles was proposed based on labeled experiments and key intermediates detected by mass spectrometry. The method highlights nickel(II)-controlled cyclization, atom-economical reaction, broad substrate scope, good functional group tolerance, and high Z-stereoselectivity.
Article
Chemistry, Organic
Dongqiu Li, Fang Cheng, Yuhai Tang, Jing Li, Yang Li, Jiao Jiao, Silong Xu
Summary: The method described involves a phosphine-catalyzed internal redox [4 + 2] annulation of 1,4-enynoates with electron-deficient alkenes, resulting in the efficient synthesis of highly functionalized cyclohexenes with exclusive regioselectivity and high diastereoselectivity under mild conditions.
Review
Chemistry, Applied
Yi-Chao Li, Yu-Hao Wang, Subarna Jyoti Kalita, Yi-Yong Huang
Summary: This review summarizes the recent advancements in nucleophilic phosphine catalysis for incorporating fluorine/s or fluoroalkyl group/s into organic molecules, focusing on the methodological progress of cycloaddition, addition, and coupling reactions using fluorinated building blocks as electrophilic and/or nucleophilic partners. The article highlights the synthetic strategies, proposed reaction mechanisms, and synthetic utilities of these organofluorine compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Zhenjie Gan, Ke Li, Hui Zhang, Er-Qing Li
Summary: A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides is reported in this study, providing optically active spiro[dihydronaphthalene-2,3'-pyrrolidine]s with one spiro quaternary and three tertiary stereogenic centers in good yields and high ee values. This protocol demonstrates high diastereo- and enantioselectivity, broad substrate scope, and mild reaction conditions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Ke Li, Zhenjie Gan, Er-Qing Li, Zheng Duan
Summary: A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Article
Chemistry, Organic
Siming Jia, Mengmeng Ma, Er-Qing Li, Zheng Duan, Francis Mathey
Summary: Two novel diastereoisomeric P-chirogenic phosphine catalysts, JiaPhos, were successfully synthesized from inexpensive starting materials in five chemical operations on a 4.16g scale. These catalysts demonstrated excellent performance in enantioselective (4 + 2) annulations, providing a diverse range of 3,3'-spirocyclic oxindoles with high efficiency and enantioselectivity.
Review
Chemistry, Multidisciplinary
Yinggao Meng, Lihui Chen, Er-Qing Li
Summary: Lewis base catalysis provides powerful synthetic strategies for the selective construction of carbon-carbon and carbon-heteroatom bonds. The nucleophilicity and steric hindrance of Lewis base catalyst often plays a major role in catalytic reactivity and selectivity in the reaction. Tremendous progress has been made in the divergent construction of valuable motifs under Lewis base catalysis in the past decades.
Article
Chemistry, Multidisciplinary
Manman Song, Jing Zhao, Er-Qing Li
Summary: This review provides a comprehensive and updated summary of the use of tertiary amine Lewis bases as catalysts for annulation reactions of allenoates. The review highlights diverse reactivities, chemoselectivities, and detailed reaction mechanisms.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Yinggao Meng, Qian Wang, Xinyu Yao, Donghui Wei, Ying-Guo Liu, Er-Qing Li, Zheng Duan
Summary: We developed novel shackled P-chiral ligands for palladium-catalyzed (4+2) annulations, producing enantioenriched tetrahydropyran scaffolds with high site selectivity and enantioselectivity. Moreover, chemoselective (4+4) products were also achieved using acyclic imines. Density functional theory calculations indicated that the reactions were mostly under thermodynamic control.
Article
Chemistry, Multidisciplinary
Qian Wang, Yinggao Meng, Lulu Wu, Er-Qing Li
Summary: Metal/nucleophilic Lewis base dual catalysis has been recognized as a reliable and promising strategy for finishing ideal organic synthesis. This new strategy expands the synthetic utility of chemical transformations by leveraging additional activation modes and has made considerable progress in the synthesis of a wide range of heterocyclic and biologically active compounds. In this review, the comprehensive and updated advances of metal/nucleophilic Lewis base dual catalytic annulation reactions are described, along with the highlighting of the related mechanism and application in natural product total synthesis.
CHINESE CHEMICAL LETTERS
(2023)
Review
Chemistry, Multidisciplinary
Mengyan Guo, Panke Zhang, Er-Qing Li
Summary: Palladium-catalyzed allylation cyclization reactions have become an important synthetic method for the construction of diverse organic compounds. This review focuses on the development of palladium-catalyzed [4 + n] cycloaddition reactions using allylic motifs, highlighting the mechanism and application of these strategies in natural product synthesis.
TOPICS IN CURRENT CHEMISTRY
(2023)
Article
Chemistry, Organic
Yinggao Meng, Manman Song, Yue Wang, Yuxin Wang, Er-Qing Li
Summary: A palladium-catalyzed asymmetric (4 + 3) cycloaddition was developed for the enantioselective synthesis of trifluoromethylated spirooxindoles. The reaction proceeded smoothly in a one-pot manner without the need for a Bronsted base, providing a cost-effective and efficient strategy for the construction of optically pure medium-sized rings.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Li Jing, Zhong-Jun Li, Er-Qing Li
Summary: We have developed a new 1,3-bis-electrophilic motif and applied it in palladium-catalyzed (3 + 2) annulations. This method offers a straightforward approach to constructing functionalized pyrrolidines with good yields. Importantly, the configuration (Z/E) of the 1,3-bis-electrophilic motif does not affect the yield and chemoselectivity of the reaction. Furthermore, preliminary asymmetric investigations using Pd(0)/thiourea synergistic catalysis resulted in moderate enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Applied
Qing-Feng Li, Jing Ma, Junjia Meng, Er-Qing Li
Summary: Nucleophilic Lewis base catalysis has emerged as an efficient method for the construction of diverse spirooxindoles. This review summarizes and classifies three catalytic strategies and highlights their applications in natural product synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Yue Wang, Jinzan Feng, Er-Qing Li, Zhenhua Jia, Teck-Peng Loh
Summary: This review summarizes the recent advances in chemo-, regio- and stereodivergent reactions catalyzed by palladium complexes. Various reaction types and probable mechanisms are discussed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yue Wang, Er-Qing Li, Zheng Duan
Summary: The development of stereodivergent strategies in asymmetric synthesis is crucial for accessing the full range of stereoisomers in products with multiple stereocenters. In this study, a novel P-chirogenic ligand, YuePhos, was developed to achieve precise switching of product stereochemistry in a Pd-catalyzed asymmetric cycloaddition reaction. The method provides an efficient route for the synthesis of pyrrolidines with up to three adjacent stereocenters, with excellent enantiomeric excesses.
Article
Chemistry, Organic
Zhipeng Zhang, Li Jing, Er-Qing Li, Zheng Duan
Summary: The study achieved (4 + 1) annulations of isatin derivatives with [2-(hydroxymethyl)allyl] carbonates using a cooperative palladium/P(NEt2)(3) system, leading to an extensive library of highly structurally diverse spirooxindole derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Materials Science, Multidisciplinary
Qing-Feng Li, Hongjun Xia, Erqing Li, Jin-Tao Wang, Zhenling Wang
Summary: This study successfully synthesized a hybrid material that can control luminescence through light stimuli, achieving the switching of luminescence of Eu3+ ions between ON and OFF states through repeated cycles of UV and visible light irradiation. This opens the possibility of developing lanthanide-based photoswitches for optical anti-counterfeiting and data storage.
JOURNAL OF MATERIALS CHEMISTRY C
(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)
