Article
Chemistry, Physical
Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang
Summary: In this study, a cross-electrophile strategy was successfully applied to synthesize multisubstituted allenes. Nickel-catalyzed reductive cross-coupling between propargyl carbonates and organoiodides provided a method to prepare tri- or tetrasubstituted allenes without the need for pregenerated organometallics. Furthermore, propargyl carbonates were found to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation, leading to the formation of chiral benzene-fused cyclic compounds with a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.
Article
Chemistry, Organic
Zhehui Liao, Jiantao Zhang, Tongxiang Cao, Shifa Zhu
Summary: A series of highly strained bicyclo[3.n.1]alkenones have been successfully synthesized with good-to-excellent enantioselectivities and moderate-to-good yields via copper-catalyzed formal [3+3] cycloaddition. The versatile chiral cycloadducts could be selectively converted into various valuable bridge systems, showing great potential for the construction of natural and bioactive compounds containing a [3.n.1] moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Christian D. -T. Nielsen, Filip G. Zivkovic, Franziska Schoenebeck
Summary: The study reported a synthetic method for N-trifluoromethyl alkynamides and found that this synthetic compound can serve as a platform to unlock access to other valuable derivatives.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wang Yao, Chuan-Jun Lu, Li-Wen Zhan, Yi Wu, Jia Feng, Ren-Rong Liu
Summary: In this study, a palladium-catalyzed enantioselective C-H activation method for pyrroles was reported, which successfully synthesized structurally diverse indole-pyrrole atropisomers with a chiral N-N axis, showing high yields and enantioselectivities. Furthermore, the kinetic resolution of trisubstituted N-N heterobiaryls with more sterically demanding substituents was also achieved. This versatile method enables the rapid and selective functionalization of pyrroles, facilitating the synthesis of valuable and complex N-N atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Vladimir A. Motornov, Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, Sema L. Ioffe
Summary: A new efficient method for the synthesis of multifunctionalized pyrrolidines via copper-catalyzed diastereoselective [3 + 2]-cycloaddition was developed, leading to the formation of novel fluorinated heterocycles like beta-fluoro-beta-nitropyrrolidines. The products exhibited good to excellent yields and high diastereoselectivity, and subsequent transformations resulted in the synthesis of medicinally attractive beta-fluoro-NH-pyrroles and other derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Hai-Tao Yang, Su-Qing Zhou, Dan-Mei Chen, Zi-Jun Hu, Xiao-Qi Qiang, Xiao-Qing Song, Sheng Tan, Wei-Hua Jiang, Yong-Qiang Sun, Chun-Bao Miao
Summary: A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed, providing a concise synthesis of 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling. 2-Alkyl cyclic 1,3-diones undergo C-C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C-O radical coupling.
Article
Chemistry, Organic
Dattatri, Maneesh Kumar Reddy Singam, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: A cascade reaction of enynones with enaminones via carbene insertion and aryl migration is reported in this study, which efficiently constructs distinctive multisubstituted furans with an all-carbon quaternary center. The protocol can be extended to synthesize furano-pyrrole bis-heterocycles in the same pot. The heterogeneity of this reaction was demonstrated by generating divergent chemical space under relatively mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Leiqing Fu, Jie-Ping Wan, Liyun Zhou, Yunyun Liu
Summary: In this study, a copper-catalyzed annulation of enaminones with alkynyl esters was developed for the synthesis of different pyrroles with a 2,3,4,5-tetrasubstituted structure. By using Cu(OAc)(2) as the catalyst, the synthesis of 2-vinyl and 2,3-dicarboxyl-functionalized pyrroles was achieved using terminal and internal alkynyl esters, respectively. The synthesis of 2-vinyl pyrroles represents the first example of accessing 2-vinyl substituted pyrroles via direct cascade reactions involving vinylation and pyrrole ring formation.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Giovanni Centonze, Chiara Portolani, Paolo Righi, Giorgio Bencivenni
Summary: Axially chiral compounds, once viewed as merely a laboratory curiosity, have gained recognition in the past two decades for their significant role in medicinal, biological, and material chemistry. The asymmetric synthesis of atropisomers, particularly N-N atropisomers, has become a rapidly expanding field with new challenges and frontiers. This review highlights recent advances and breakthroughs in the enantioselective synthesis of N-N atropisomers, showcasing the strategies and frameworks involved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chi Bong Eric Chao, Stephen G. Pyne, Christopher J. T. Hyland, Richmond Lee
Summary: Density functional theory has been used to elucidate the mechanistic details of arylative cyclization reactions with arylboronic acids. The modeling results are in agreement with experimental observations and explain the high diastereo- and enantioselectivity at high reaction temperature. Additionally, a novel mechanism for base-free organoboron transmetalation has been revealed.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Yuan Zhao, Ningning Liu, Shiping Zhong, Ziwei Wen, Tao Wang
Summary: This article presents a strategy for central-to-axial chirality conversion via a gold(I)-catalyzed 5-endo-dig cyclization/dehydration cascade to construct C-N axially chiral N-arylpyrroles from amino acid derivatives. The reaction demonstrates high efficiency in central-to-axial chirality conversion.
Article
Chemistry, Organic
Jin-Wei Yuan, Chen-Xu Mou, Yang Zhang, Wen-Yu Hu, Liang-Ru Yang, Yong-Mei Xiao, Pu Mao, Shou-Ren Zhang, Ling-Bo Qu
Summary: This practical synthetic route utilizes transition-metal Cu/Ag-catalyzed oxidative ipso-annulation of activated alkynes with unactivated toluenes using TBPB as an oxidant under microwave irradiation to construct a variety of 3-benzyl spiro[4,5]trienones. The method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-carbocyclization, and dearomatization. Its advantages include operational simplicity, broad substrate scope, and the ability to afford the desired products in moderate to good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Liting Hou, Wenyi Huang, Xianqing Wu, Jingping Qu, Yifeng Chen
Summary: Herein, we presented a Ni-catalyzed carbonylation of cyclopropanol and benzyl bromide to synthesize multisubstituted cyclopentenones. The reaction involves cascade carbonylation, generation of nickel homoenolate from cyclopropanols, and intramolecular Aldol condensation.
Article
Biochemistry & Molecular Biology
Huimin Wang, Shuqin Zhang, Minling Xu, Gang Zou
Summary: Researchers have developed a practical and efficient Suzuki coupling reaction of phenols using trans-NiCl(o-Tol)(PCy3)(2)/2PCy(3) as a catalyst and tosyl fluoride as an activator. The compatibility of the nickel catalyst with tosyl fluoride and its fluorosulfate exchange reaction with C-Ar-OH are crucial for the direct use of phenols. Water improves the one-pot reaction significantly, and a variety of electronically and sterically diverse biaryls can be obtained in good yields using 3-10 mol% of the nickel catalyst.
Article
Chemistry, Organic
Lvyin Zheng, Liuhuan Cai, Weijie Mei, Gongping Liu, Ling Deng, Xiaoying Zou, Xiaoya Zhuo, Yumei Zhong, Wei Guo
Summary: In this study, an efficient copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction was developed for the synthesis of multisubstituted phosphorylhydrazides. The reaction proceeded under mild conditions without the need for any external oxidants and bases. The selected compounds exhibited potential inhibitory activity against tumor cells, making them suitable for the screening of anticancer agents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Simone M. Gillbard, Hon Wai Lam
Summary: The use of arylboron reagents in metal-catalyzed domino addition-cyclization reactions is an important synthetic strategy for the preparation of diverse, highly functionalized carbo- and heterocyclic products. Recent studies have shown that nickel catalysts offer unique reactivity and access to products that are otherwise difficult to obtain.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Joshua Humphreys, Ferdinando Malagreca, Paul Hume, William Lewis, E. Stephen Davies, Stephen P. Argent, David B. Amabilino
Summary: The study reports on a series of N-alkylated PyrDPP dyes and their properties in solution and in the solid state, showing that the nature of the chain affects the molecular packing and absorption spectra in the solid state, with different chain dyes exhibiting variations in charge transfer performance.
Article
Chemistry, Multidisciplinary
Luke O'Brien, Stephen P. Argent, Kristaps Ermanis, Hon Wai Lam
Summary: Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates were studied. The reactions showed high selectivity and provided a variety of functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Experimental evidence and density functional theory calculations revealed the mechanistic insights.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Andrew J. Valentine, Laurence J. Taylor, Ana M. Geer, Cameron D. Huke, Katherine E. Wood, Will Tovey, William Lewis, Stephen P. Argent, Andrew M. Teale, Jonathan McMaster, Deborah L. Kays
Summary: The effects of para-substitution on the structural and electronic properties of two-coordinate m-terphenyl Group 12 complexes have been investigated. X-ray crystallography shows little structural variation, but considerable electronic differences are revealed by heteronuclear NMR spectroscopy. Density functional theory calculations are used to rationalize these trends.
Article
Chemistry, Physical
Marina A. Tokareva, Indrek Pernik, William Lewis, Barbara A. Messerle, Tatiana Glukhareva, Sinead T. Keaveney
Summary: In this study, ligand-controlled rhodium(I)-catalyzed denitrogenative transformations of different types of 4-vinyl-1,2,3-thiadiazoles were demonstrated. With [Rh(COD)(2)]BF4, vinylic 1,2,3-thiadiazoles undergo intramolecular transannulation reaction to afford substituted furans. However, with [Rh(COD)DPPF]BF4, intermolecular transannulation reaction occurs, providing access to highly functionalized thiophenes.
Article
Chemistry, Multidisciplinary
Dmitry Gorbachev, Elliot Smith, Stephen P. Argent, Graham N. Newton, Hon Wai Lam
Summary: This study describes the synthesis of new morphinan opioids by adding photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring. By using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the feasibility of late-stage modification of complex, highly functionalized substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Magdalene W. S. Chong, Stephen P. Argent, Florian Moreau, William J. F. Trenholme, Christopher G. Morris, William Lewis, Timothy L. Easun, Martin Schroder
Summary: In this study, a 2D coordination network with a unique structure was synthesized, and its strong selectivity for different gases was discovered.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Multidisciplinary Sciences
Xin Wu, Patrick Wang, William Lewis, Yun-Bao Jiang, Philip A. Gale
Summary: This study investigates the quantification of anion binding within lipid bilayers using a fluorescent macrocycle with strong sulfate affinity. The authors discover that the determinants of anion binding in lipid bilayers differ from those in solution. These findings provide insights into the principles of anion binding within lipid bilayers and have implications for the design of functional molecular systems at biomembrane interfaces.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Eleanor R. Kearns, Jack K. Clegg, William Lewis, Ada Fang, Bun Chan, Deanna M. D'Alessandro
Summary: As complex materials are widely used in emerging technologies for environmental and energy applications, it is important to be able to quantify their stimuli-response behaviors. In this study, a double [2 + 2] photocyclization reaction in a photoactive material was utilized as a powerful platform to quantitatively investigate solid-state photocyclization kinetics. The results showed a maximum rate observed between 0 degrees C and 20 degrees C of approximately 0.172 s-1, providing the first example of quantification of photocyclization kinetics in a MOF. Density functional theory calculations supported a singlet reaction mechanism for the double [2 + 2] photocyclization.
CHEMISTRY OF MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Max Roemer, William Lewis
Summary: Copper nanostructures were obtained by reducing Cu(I) under mild conditions in ethanol/water using sodium-l-ascorbate and sodium azide in an amination reaction. When reacting the halobenzene substrate in the presence of a bulk carbon black support, clustered copper sub-micrometer particles (SMPs) and microparticles (MPs) were formed. The supported nanostructures were characterized and found to be active catalysts in the azide-alkyne cycloaddition (CuAAC). The catalytic competency of the particles was assessed and optimized conditions were used for the synthesis of triazole compounds.
Article
Chemistry, Inorganic & Nuclear
Roberto Nolla-Saltiel, Ana M. Geer, Helen R. Sharpe, Cameron D. Huke, Laurence J. Taylor, Thomas G. Linford-Wood, Ashleigh James, Jamie Allen, William Lewis, Alexander J. Blake, Jonathan Mcmaster, Deborah L. Kays
Summary: This study reports the synthesis of ruthenium complexes with phosphinocarboxamide ligands and their use in forming metallacycles through halide abstraction/deprotonation reactions. The coordination and structure of these complexes were studied using X-ray diffraction and NMR spectroscopy, revealing the presence of intramolecular hydrogen bonding and rotational isomers in solution.
Article
Chemistry, Inorganic & Nuclear
Andrew J. Valentine, Ana M. Geer, Toby J. Blundell, Will Tovey, Matthew J. Cliffe, E. Stephen Davies, Stephen P. Argent, William Lewis, Jonathan McMaster, Laurence J. Taylor, Daniel Reta, Deborah L. Kays
Summary: Five structurally related two-coordinate Fe(II) m-terphenyl complexes were studied, and it was found that changing the functionalization of the ligand can alter their magnetic function. Using more electron donating R groups can slow down the rate of magnetic relaxation.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Hunter J. Windsor, William Lewis, Suzanne M. Neville, Samuel G. Duyker, Deanna M. D'Alessandro, Cameron J. Kepert
Summary: A 3D Hofmann-like metal-organic framework with a 2,1,3-benzothiadiazole-based pillaring ligand has been synthesized. The encapsulation of a polycyclic aromatic hydrocarbon, chrysene, within the pore structure enables a new pathway to multi-step spin crossover behavior, where the observed two-step spin transition is attributed to the presence of multiple site environments and local guest positional effects within the host lattice.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xiaochen Fu, Matthew Sale, Bowen Ding, William Lewis, Debbie S. Silvester, Chris D. Ling, Deanna M. D'Alessandro
Summary: A new enzyme-free glucose sensor with robustness, accuracy, and high sensitivity was developed in this study. The sensor shows improvement in operational flexibility compared to traditional systems, with the additional advantage of low sample loadings.
Article
Chemistry, Multidisciplinary
Simone M. Gillbard, Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are discussed in this study.
CHEMICAL COMMUNICATIONS
(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)
