Article
Chemistry, Physical
Pavol Lopatka, Michal Gavenda, Martin Markovic, Peter Koos, Tibor Gracza
Summary: This work describes the total synthesis of jaspine B using highly diastereoselective Pd(II)-catalysed carbonylative cyclisation for the preparation of crucial intermediates. New conditions involving the use of pBQ/LiCl and Fe(CO)(5) were developed, and the application of a flow reactor in large-scale preparation of key lactones was demonstrated.
Article
Chemistry, Applied
Xu Wang, Jin-Ping Fu, Jia-Hui Mo, Yu-Hong Tian, Chun-You Liu, Hai-Tao Tang, Zi-Jun Sun, Ying-Ming Pan
Summary: The palladium-catalysed tandem cyclisation reaction successfully synthesizes a variety of 5-aminoimidazoles under mild conditions with high yields. This elegant domino process involves the effective cleavage of the N-O bond and the formation of new C-C and C-N bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Mengning Wang, Qiuzhu Wang, Mengtao Ma, Binlin Zhao
Summary: A copper-catalysed synthesis of trifluoromethyl allenes has been developed, providing a simple and practical platform for the preparation of substituted allenes with a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Sean R. Barlow, Lily J. Callaghan, Vilius Franckevicius
Summary: The palladium-catalysed cyclisation of propargylic electrophiles with nucleophiles is a useful synthetic approach for the rapid construction of heterocyclic building blocks, but it poses challenges in controlling the chemo-, regio- and stereoselectivity simultaneously. The discovery of alpha-amido malonates as novel bis-nucleophiles in this reaction has shown high chemo- and regioselectivity, as well as moderate enantioselectivity in the formation of functionalised dihydrooxazine heterocycles, expanding the range of available heterocycles for medicinal chemists.
Article
Chemistry, Applied
Anastasia Kurbanova, Martin Nigrini, Kinga Golabek, Ondrej Vesely, Jan Vesely
Summary: Synthetic organic chemistry often requires multiple steps and expensive catalysts for the synthesis of functionalised tetrahydropyrans. In this study, we tested zeolites as eco-friendly and industrially relevant catalysts for the synthesis of 2-phenyltetrahydropyran. The results showed that zeolites favor the formation of the desired product, and the reaction kinetics depend on the number of acid sites, rather than the textural properties.
MICROPOROUS AND MESOPOROUS MATERIALS
(2023)
Article
Chemistry, Applied
Hui-Shu Lin, Yong-Zhou Pan, Yu-Hong Tian, Ying-Ming Pan, Xu Wang
Summary: A Pd-catalyzed tandem cyclization reaction has been developed, allowing the efficient construction of new C-C and C-N bonds via the orderly insertion of isocyanides. Various indeno[2,1-b]pyrroles were prepared in moderate to high yields under air atmosphere at 100°C.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ran Ding, Ya-Li Liu, Hui Hao, Chuan-Yi Chen, Lei Liu, Nian-Shou Chen, Yu Guo, Pei-Long Wang
Summary: A copper(I)-catalyzed sulfonylation-cyclization method has been developed for the transformation of 1,5-dienes with sulfonyl chlorides. The reaction exhibits a wide substrate scope and excellent regioselectivity, resulting in the formation of derivatized 1,5-dihydro-2H-pyrrol-2-one scaffold in one pot.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Luomo Li, Sascha Kail, Sebastian M. Weber, Gerhard Hilt
Summary: Indium tribromide catalyzed the transfer hydrogenation from dihydroaromatic compounds to enones, resulting in the cyclisation to trisubstituted furan derivatives. Protonation from the Wheland complex led to the formation of the product, replacing the indium tribromide substituent. Site-specific deuterium labelling of the dihydroaromatic HD surrogates provided insights into the reaction mechanism by H-D scrambling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Zhen Yang, Rene M. Koenigs
Summary: A conceptually distinct approach was developed for the dicarbofunctionalization of alkynes at room temperature using simple alkyl iodides and a second molecule of alkyne as coupling partner. This method enables the one-step synthesis of 1,3-enynes with high efficiency without the need for exogenous photosensitizers or oxidants, paving the way for cascade reactions via photochemical palladium catalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Subir Panja, Salman Ahsan, Tanay Pal, Simon Kolb, Wajid Ali, Sulekha Sharma, Chandan Das, Jagrit Grover, Arnab Dutta, Daniel B. Werz, Amit Paul, Debabrata Maiti
Summary: This study reports a new non-directed and regioselective olefination method for simple arenes via an electrooxidative catalytic cycle, demonstrating a wide substrate scope.
Article
Chemistry, Physical
Naba Abuhafez, Herve Ruffin, Raghu Kamaraj, Christian Bruneau, Rafael Gramage-Doria
Summary: A new method for the synthesis of 1,3-diene building blocks using ruthenium-catalyzed oxidative homo- and cross-coupling is reported, which mainly produces the E,E isomer. This methodology also allows for the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Applied
Li-Yun Guo, Qing Li, Yu-Tao Liu, Lin Li, Yu-Qing Ni, Yang Li, Fei Pan
Summary: A palladium-catalyzed method for direct alkynylation of unactivated alkenes via C-H activation, assisted by 8-aminoquinoline, has been successfully developed. This method is applicable to both internal and terminal unactivated alkenes, showing broad functionality tolerance, good regio- and diastereoselectivity, and providing an alternative approach for constructing conjugated 1,3-enynes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Suchen Zou, Zeyu Zhao, Hanmin Huang
Summary: In this study, a novel and efficient palladium-catalyzed reaction was developed for the regioselective and stereodivergent ring-closing of aminoenynes with aldehydes and boronic acids or hydrosilane. The reaction allows for the synthesis of a series of exocyclic 1,3-dienes bearing saturated N-heterocycles of 5- to 8-membered rings. It utilizes a simple Pd-catalyst and works under mild reaction conditions with a broad range of substrates. The resulting products serve as useful intermediates for chemical synthesis due to the versatility of the conjugated diene. Preliminary mechanistic details of the reaction are also uncovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ming Li, Guo-Qing Sun, Yu-Yu Liu, Shun-Xi Li, Hai-Chao Liu, Yi-Feng Qiu, Dong-Pin Chen, Xi-Cun Wang, Yong-Min Liang, Zheng-Jun Quan
Summary: A nickel-catalyzed three-component tandem radical cyclization reaction was developed to synthesize gamma-lactam-substituted allene derivatives from aryl bromides, 1,3-enynes, and aryl boric acids. This strategy allowed the lactam alkyl radicals generated through the cyclization process to participate in multicomponent coupling, leading to the direct conversion of 1,3-enynes into poly substituted allene compounds. The method demonstrated wide substrate scope and provided a series of 1,5-difunctionalized allenes in a one-pot reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fangyuan Zhang, Florian Rauch, Asim Swain, Todd B. Marder, Prince Ravat
Summary: This article introduces a design strategy to achieve narrow-band emission for applicable circularly polarized luminescence (CPL) active materials in ultrahigh-definition CP-OLEDs, by exploiting intramolecular donor-acceptor interactions between nitrogen and boron atoms. Single- and double-helicenes with 1,4-B,N-embedded configurationally stable structure were successfully synthesized, showing unprecedentedly narrow fluorescence and CPL bands, along with high fluorescence quantum yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yuan-He Li, Su-Lei Zhang, Yong Lu, Bo Xiao, Tian-Yu Sun, Qian-Qian Xu, Jia-Hua Chen, Zhen Yang
Summary: A highly enantioselective catalytic system for exo-Diels-Alder reactions was developed using bispyrrolidine diboronates(BPDB). Activated by various Lewis or Bronsted acids, BPDB can catalyze highly stereoselective asymmetric exo-Diels-Alder reactions. The catalyst can also distinguish between different binding sites to achieve highly regioselective reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hamad H. Al Mamari, Julie Borel, Aobha Hickey, Eimear Courtney, Julia Merz, Xiaolei Zhang, Alexandra Friedrich, Todd B. Marder, Gerard P. McGlacken
Summary: The quinolone-quinoline tautomerization is utilized to achieve regioselective C8-borylation of biologically important 4-quinolones. This is done by using [Ir(OMe)(cod)](2) as the catalyst precursor, the silica-supported monodentate phosphine Si-SMAP as the ligand, and B(2)pin(2) as the boron source. The resulting C8-borylated quinolines can be further converted to various derivatives with different substituents.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Arvind Barak, Nishant Dhiman, Floriane Sturm, Florian Rauch, Yapamanu Adithya Lakshmanna, Karen S. Findlay, Andrew Beeby, Todd B. Marder, Siva Umapathy
Summary: The compound DACM-DPA exhibits significant charge transfer character in the excited state in polar solvents. Transient absorption measurements show different excited-state lifetimes in n-hexane, acetonitrile, and methanol. Raman measurements reveal the structural dynamics and the formation of an intramolecular charge-separated state.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Organic
Jianguo Hu, Shengchun Wang, Bin Li, Aiwen Lei
Summary: We report a protocol for constructing tetrahydroquinolines from bulk chemicals (alkenes and anilines) induced by K2S2O8. The method exhibits operational simplicity, wide scope, mild conditions, and a transition-metal-free system.
Article
Chemistry, Organic
Chang-Ming You, Cheng Huang, Sheng Tang, Peng Xiao, Shengchun Wang, Zhenhong Wei, Aiwen Lei, Hu Cai
Summary: Direct N-allylation of azoles with hydrogen evolution has been achieved by the synergistic combination of organic photocatalysis and cobalt catalysis. This protocol eliminates the need for stoichiometric oxidants and prefunctionalization of alkenes, and produces hydrogen (H2) as a byproduct. The transformation highlights high step and atom economy, high efficiency, and broad functional group tolerance, opening up a pathway for valuable C-N bond formation in heterocyclic chemistry.
Article
Multidisciplinary Sciences
Dongfeng Yang, Zhipeng Guan, Yanan Peng, Shuxiang Zhu, Pengjie Wang, Zhiliang Huang, Hesham Alhumade, Dong Gu, Hong Yi, Aiwen Lei
Summary: By electrochemical oxidative difunctionalization, the authors achieved functionalization of diazo compounds with two different nucleophiles. This method allows the synthesis of structurally diverse heteroatom-containing compounds, which are difficult to access by traditional methods, and display important synthetic applications. The reaction conditions are mild, exhibiting excellent functional group tolerance and efficiency for large-scale synthesis.
NATURE COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Wuyin Wang, Wentao Mo, Zishan Hang, Yueying Huang, Hong Yi, Zhijun Sun, Aiwen Lei
Summary: Transition metal element, copper, plays diverse and pivotal roles in oncology. It acts as constituents of metalloenzymes involved in cellular metabolism, function as signaling molecules to regulate the proliferation and metastasis of tumors, and are integral components of metal-based anticancer drugs. Notably, recent research reveals that excessive copper can also modulate the occurrence of programmed cell death (PCD), known as cuprotosis, in cancer cells.
Review
Chemistry, Multidisciplinary
Li Zeng, Jianxing Wang, Daoxin Wang, Hong Yi, Aiwen Lei
Summary: Organic electrosynthesis using alternating current (AC) is still in its early stages due to the lack of a comprehensive theoretical framework. This article provides an overview of recent advancements in AC-driven organic transformations and explores the differences between DC and AC electrolytic methodologies based on their physical principles. These differences include the prevention of metal catalyst deposition, precise modulation of oxidation and reduction intensities, and mitigation of mass transfer processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lukas Tendera, Laura Kuehn, Todd B. Marder, Udo Radius
Summary: The synthesis of the first terminal mono-boryl complexes of nickel, without a pincer ligand, is reported. Various reactions were conducted to exchange ligands and obtain the desired nickel mono-boryl complexes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Hao-Yuan Liu, Zhen-Yu Zhang, Yi-Ke Zhou, Jia-Hua Chen, Zhen Yang, Yuan-He Li
Summary: This paper presents an efficient strategy for synthesizing the DEFGH rings of phainanoid F, involving a photo-induced electrocyclization and a homoallylic elimination. It is noteworthy that the electrocyclization reaction was used to simultaneously construct two vicinal quaternary carbons in total synthesis, which is a rare example. The strategy outlined here serves as the basis for the total synthesis of Phainanoid F and could be applied in synthesizing other natural products with similar 13,30-cyclodammarane skeletons.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Zhenyu Zhang, Wei Zhang, Jun-Chen Tang, Jin-Teng Che, Zhongchao Zhang, Jia-Hua Chen, Zhen Yang
Summary: The researchers synthesized (+)-Haperforin G in 20 steps from commercially available starting materials. They used a Co-catalyzed intramolecular Pauson-Khand reaction to selectively construct a cyclopentanone with an all-carbon quaternary stereogenic center at the bridge-head position. Light-initiated photocatalysis was employed for the convergent and asymmetric cross-coupling of the unstabilized C(sp(3)) radical with an enone. This developed chemistry opens up possibilities for synthesizing structurally diverse analogs of haperforin G (6).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jiefeng Hu, Man Tang, Jing Wang, Zhu Wu, Alexandra Friedrich, Todd B. Marder
Summary: We report the design and synthesis of a stable, multifunctional (diborylmethyl)iodide reagent for the photoinduced cyclopropanation of alkenes, providing an array of 1,2-substituted cyclopropylboronates in good yields. The protocol displays high chemo- and diastereoselectivity, excellent functional-group tolerance, and allows for late-stage borylcyclopropanation of complex molecules. Mechanistic studies reveal that the borylcyclopropanation proceeds through a radical addition/polar cyclization pathway mediated by the photocatalyst fac-Ir(ppy)(3) and visible light.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jinming Wang, Yichang Liu, Xupeng Zong, Aiwen Lei, Zaicheng Sun
Summary: Photochemistry has become increasingly important in organic synthesis and heterogeneous photocatalysts have advantages over traditional homogeneous photocatalysts in terms of production, separation, catalyst recycling, and stability. In this review, the development and advantages of a heterogeneous catalytic system for C-N bond formation as a typical coupling reaction are summarized. Important heterogeneous photocatalysts such as titanium dioxide, semiconductor quantum dots, covalent organic frameworks, and carbon nitrides are discussed in detail. The combination and electron transfer pathway between heterogeneous catalysts and transition-metal catalysts are the focus of this review. These advances not only apply to C-N coupling, but also extend to other coupling reactions.
Article
Chemistry, Multidisciplinary
Yiran Xu, Shengchun Wang, Zhao Liu, Mian Guo, Aiwen Lei
Summary: A photo/nickel dual-catalyzed defluorinative sulfonylation method has been developed to synthesize gem-difluoro allylsulfones rapidly and reliably. This protocol demonstrates mild conditions and a wide scope, providing a novel strategy for the sulfonyl radical participating in radical defluorinative coupling.
CHEMICAL COMMUNICATIONS
(2023)
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)
