Article
Chemistry, Multidisciplinary
Michael J. Tilby, Damien F. Dewez, Adrian Hall, Carolina Martinez Lamenca, Michael C. Willis
Summary: In this study, the absolute configuration of sulfur-stereogenic aza-sulfur derivatives was determined using a unique feature of sulfonimidamides. Enantioselective alkylation was achieved by generating prochiral ions from sulfonimidamides with the help of a bis-quaternized phase-transfer catalyst. This demonstrates the potential of using configurationally labile aza-sulfur species in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zhibin Guo, Daehyun Oh, Min Sagong, Jewon Yang, Geumwoo Lee, Hyeung-geun Park
Summary: An efficient method for synthesizing chiral malonates was established using enantioselective phase transfer catalysis. The a-alkylation reaction of 2,2-diphenylethyl tert-butyl a-methylmalonates with (S,S)-3,4,5-trifluorophenyl-NAS bromide as a phase-transfer catalyst successfully yielded corresponding a-methyl-a-alkylmalonates. These compounds are versatile chiral building blocks with a quaternary carbon center, obtained in high chemical yields (up to 99%) and excellent enantioselectivities (up to 98% ee). Selective hydrolysis of a,a-dialkylmalonates to the corresponding chiral malonic monoacids was achieved using basic (KOH/MeOH) and acidic conditions (TFA/CH2Cl2), demonstrating the practicality of the method.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinduo Sun, Chaoji Xiong, Fanrui Zhou, Kun Liang, Chunhua Wu, Xiaoping Rao, Qian Chen
Summary: The asymmetric addition of terminal alkynes catalyzed by a transition metal to isatins is an efficient and economical method for synthesizing 3-alkynyl-3-hydroxy-2-oxindoles. Using a new dimeric chiral quaternary ammonium derived from quinine as the cationic inducer, under mild conditions, the desired chiral compounds can be obtained in good to high yields with high enantioselectivity (<= 99% ee), and a variety of aryl-substituted terminal alkynes and substituted isatins are tolerated in this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrew T. Champlin, Jonathan A. Ellman
Summary: Sulfur alkylation of N-acyl sulfenamides with alkyl halides leads to sulfilimines, with yields ranging from 47% to 98%. This reaction demonstrates a wide scope with different aryl and alkyl sulfenamides, as well as various N-acyl groups. Alkyl halides with different steric and electronic properties, including methyl, primary, secondary benzyl, and propargyl halides, are effective reactants. Furthermore, an asymmetric phase-transfer alkylation was successfully demonstrated. The resulting sulfilimine products can be easily converted to N-acyl and free sulfoximine, which are important motifs in medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Arnab K. Maity, Annah E. Kalb, Matthias Zeller, Christopher Uyeda
Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xavier Abel-Snape, Gina Wycich, Mark Lautens
Summary: A palladium-catalyzed three-component domino reaction for accessing indene derivatives is described. The reaction involves the sequential formation of three bonds, with the first two resulting from inter- and intramolecular carbopalladation, and the final bond arising from an attack by a terminating nucleophilic reagent. The starting tether on the iodoarene can be modified to yield either indenes or benzofulvenes. Additionally, the use of an oxabicycle as an acetylene surrogate is demonstrated, and the enantioselective synthesis of indenes is preliminarily explored.
Article
Chemistry, Applied
Sergio Fernandez, Javier Santamaria, Alfredo Ballesteros
Summary: This study presents a simple, regioselective and high yielding gold-catalyzed synthesis of benzofulvenes using progargylsilanes and benzophenones as reactants. The silyl moiety synergistically activates the carbonyl compound, and the participation of aluminum trichloride as a cocatalyst clearly increases the gold catalytic activity in the cyclization step. Mechanistic intermediates, including enynes and silylbenzofulvenes, have been isolated, and control experiments confirm the involvement of [LAu][NTf2AlCl3] complex as the true catalyst. The coordination of the Lewis acid to the gold counterion dramatically enhances the gold activity.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Daniel Moock, Tobias Wagener, Tianjiao Hu, Timothy Gallagher, Frank Glorius
Summary: This study presents a method for enantio- and diastereoselective hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis, allowing controlled installation of up to six new defined stereocenters to produce complex octahydrobenzofurans prevalent in bioactive molecules. The unique combination of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor enables the process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Huai-Ri Sun, Atif Sharif, Jie Chen, Ling Zhou
Summary: Atropisomeric heterobiaryls have gained significant interest from chemists in recent years for their crucial role in natural products, chiral ligands, organocatalysts, and other research fields. Various optically active heterobiaryls based on indole, quinoline, isoquinoline, pyridine, pyrrole, azole, and benzofuran skeletons have been successfully synthesized through metal or organic catalytic cross-coupling, functionalization of prochiral or racemic heterobiaryls, and ring formation. This review summarizes the enantioselective synthesis of axially chiral heterobiaryls through strategies such as cycloaddition, cyclization, and chirality conversion, along with the discussion of the reaction mechanism and the corresponding applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Sheng-Suo Zhou, Xing-Yun Sun, Wen-Kai Liu, Jia-Yu Song, Zheng Wang, Zheng-Hang Qi, Xing-Wang Wang
Summary: A palladium-catalyzed regioselective and asymmetric allylic alkylation reaction using chiral oxalamide-phosphine ligands has been developed for the synthesis of optically active γ-arylidenyl glutamic acid derivatives. The reaction gives good yields with excellent regio- and enantioselectivity, and provides an alternative approach for the preparation of enantio-enriched unnatural α-amino acid derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Istvan Orban, Dora Ujj, Bela Matravolgyi, Tamas Holczbauer, Zsolt Rapi
Summary: Carbohydrate-based macrocycles can serve as enantioselective catalysts, and their catalytic activity can be influenced by the carbohydrate moiety. D-glucose and D-galactose-based crown ethers exhibit the best enantioselective properties. Incorporation of the rare monosaccharide D-idose into the macrocycle structure shows that enantioselectivity is dependent on the configuration of the anomeric center, the side arm of the nitrogen, and the substrate structure.
Review
Chemistry, Multidisciplinary
Wenchao Chen, Choon-Hong Tan, Hong Wang, Xinyi Ye
Summary: Oxidation using molybdenum/tungsten-based heteropoly salts as catalysts has attracted significant attention due to low-cost and environmentally friendly terminal oxidants. This review summarizes the recent progress in utilizing heteropoly salts for oxidations and highlights the catalytically active peroxometalate species involved in the process. The aim is to inspire further exploration in functional metalates for catalytic oxidations and understanding design principles for more efficient, selective, and economical catalytic systems.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Physical
Sung Kwon, Shawn Sandhu, Moaid Shaik, Jacob Stamm, Jesse Sandhu, Rituparna Das, Caitlin V. Hetherington, Benjamin G. Levine, Marcos Dantus
Summary: This study examines the possibility of three hydrogen atoms in one plane of the cyclopropane dication forming H-3(+) through a concerted ring-closing mechanism. Ultrafast strong-field ionization and disruptive probing measurements suggest that the formation time of H-3(+) is 249 +/- 16 fs, which is not consistent with a concerted mechanism but indicates a ring-opening process. Measurements on propene, an isomer of cyclopropane, show a similar formation time of H-3(+). Ab initio molecular dynamics simulations and a common potential energy surface support the ring-opening mechanism.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Organic
Qing-he Zhao, Guang-hao Yu, Ye-chen Meng, Feng Sui, Mi-yi Yang, Li Liu, Hui-jie Li, Feng Li, Hai Ma
Summary: A series of (trifluoromethyl)cyclopropanes have been synthesized in high yields through the cyclization reaction between nitromethane and 5-[beta-(trifluoromethyl)styryl]isoxazoles. This method, which employs an inorganic base under phase-transfer conditions, provides a practical approach for accessing the cyclopropyl moiety of pharmacological interest.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Physical
Nazanin Noroozi-Shad, Mostafa Gholizadeh, Hossein Sabet-Sarvestani
Summary: This review summarizes the important advances in the properties, synthesis, and applications of quaternary phosphonium salts as catalysts in chemical transformations and synthetic chemistry. It also discusses the applications of asymmetric phosphonium salts in enantioselective organic reactions in phase-transfer catalysis.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Bjarke S. Donslund, Alicia Monleon, Teresa A. Palazzo, Mette Louise Christensen, Anne Dahlgaard, Jeremy D. Erickson, Karl Anker Jorgensen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Bjarke S. Donslund, Nicolaj Inunnguaq Jessen, Giulio Bertuzzi, Maxime Giardinetti, Teresa A. Palazzo, Mette Louise Christensen, Karl Anker Jorgensen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Niels Hammer, Jeremy D. Erickson, Vibeke H. Lauridsen, Joakim B. Jakobsen, Bente K. Hansen, Kristian M. Jacobsen, Thomas B. Poulsen, Karl Anker Jorgensen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Review
Chemistry, Multidisciplinary
David McLeod, Mathias Kirk Thogersen, Nicolaj Inunnguaq Jessen, Karl Anker Jorgensen, Cooper S. Jamieson, Xiao-Song Xue, K. N. Houk, Fang Liu, Roald Hoffmann
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Multidisciplinary
Magnus H. Ronne, Dasol Cho, Monica R. Madsen, Joakim B. Jakobsen, Seunghwan Eom, Emile Escoude, Christian D. Hammershoj, Dennis U. Nielsen, Steen U. Pedersen, Mu-Hyun Baik, Troels Skrydstrup, Kim Daasbjerg
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Inorganic & Nuclear
Monica R. Madsen, Joakim B. Jakobsen, Magnus H. Ronne, Hongqing Liang, Hans Christian D. Hammershoj, Peter Norby, Steen U. Pedersen, Troels Skrydstrup, Kim Daasbjerg
Article
Chemistry, Organic
Alicia Monleon, Marc Montesinos-Magraner, Amparo Sanz-Marco, Gonzalo Blay, Jose R. Pedro
Editorial Material
Chemistry, Multidisciplinary
Joakim B. Jakobsen, Magnus H. Ronne, Kim Daasbjerg, Troels Skrydstrup
Summary: The reduction of carbon dioxide is crucial for producing non-fossil-fuel-based feedstocks and mitigating greenhouse gas emissions. Amines play a critical role in these transformations, acting as CO2 trapping agents, proton shuttles, electron donors, and facilitators of CO2 reductions through formamide derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Nicolaj Inunnguaq Jessen, Giulio Bertuzzi, Maksimilian Bura, Mette Louise Skipper, Karl Anker Jorgensen
Summary: The study developed an enantioselective [12+2] cycloaddition for constructing a chiral cycl[3.2.2]azine core, with focus on the reaction mechanism through combined experimental and computational investigations. The reaction exhibited excellent selectivity and yields, with robust adaptability to various electron-deficient 2π-components.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Andreu Tortajada, Jose Tiago Menezes Correia, Eloisa Serrano, Alicia Monleon, Alberto Tampieri, Craig S. Day, Francisco Julia-Hernandez, Ruben Martin
Summary: A region-divergent Ni-catalyzed amidation of unactivated secondary alkyl bromides is described in this study, with site-selectivity of the amidation event dictated by subtle differences on the ligand backbone, enabling introduction of the amide function at either the original sp(3) carbon-halide bond or at distal sp(3) C-H sites within an alkyl side-chain via chain-walking scenarios.
Article
Chemistry, Physical
Wanwan Hong, Mahika Luthra, Joakim B. Jakobsen, Monica R. Madsen, Abril C. Castro, Hans Christian D. Hammershoj, Steen U. Pedersen, David Balcells, Troels Skrydstrup, Kim Daasbjerg, Ainara Nova
Summary: Selective reduction of CO2 to produce nonfossil-based chemical feedstocks and reduce atmospheric greenhouse gas concentration is important. This study investigates how the molecular structure of Mn-based complexes determines the product selectivity in CO2 reduction. The results show that by utilizing bpy-based macrocycles, the product selectivity can be changed from formic acid to H2. This research provides atomistic details that can be used in the development of fully selective systems.
Article
Biochemistry & Molecular Biology
Ramon Jimenez-Robles, Marta Izquierdo, Vicente Martinez-Soria, Laura Marti, Alicia Monleon, Jose David Badia
Summary: Superhydrophobic PVDF membranes with high water contact angles (WCA) were achieved through oxygen plasma activation and functionalization. The surface modifications led to morphological changes and a pillar-like structure with higher surface porosity. The plasma-treated membranes maintained their superhydrophobic performance even after long-term operations.
Article
Biochemistry & Molecular Biology
Alicia Monleon, Gonzalo Blay, Jose R. Pedro
Summary: A convenient procedure for synthesizing N-carbamoyl-protected propargylic amines substituted with a cyclopropyl group from alpha-amido sulfones and cyclopropylacetylene is described. The reaction is catalyzed by a chiral BINOL-type zinc complex, providing the corresponding products in good yields and enantioselectivities.
Article
Chemistry, Multidisciplinary
Maxime Giardinetti, Nicolaj Inunnguaq Jessen, Mette Louise Christensen, Karl Anker Jorgensen
CHEMICAL COMMUNICATIONS
(2019)
Review
Chemistry, Applied
Lode De Munck, Alicia Monleon, Carlos Vila, Jose R. Pedro
ADVANCED SYNTHESIS & CATALYSIS
(2017)
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)
