Review
Chemistry, Organic
Marcos Escolano, Daniel Gavina, Javier Torres, Santiago Diaz-Oltra, Carlos del Pozo
Summary: The organocatalytic enantioselective desymmetrization reaction via intramolecular (hetero)Michael addition is an effective strategy for creating complex carbo- and heterocycles with multiple stereocenters in a simple manner. The main challenge lies in the design and synthesis of the starting materials.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Fabian Scharinger, Matthias Weil, Michael Schnuerch, Katharina Bica-Schroeder
Summary: We introduce a simple method for the synthesis of chiral diazabicycloalkanes in a single reaction step. This method is applicable to a wide range of enals and has high functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Daniel M. Day, Thomas J. Farmer, James Sherwood, James H. Clark
Summary: This study investigates the reactivity of dimethyl itaconate as a bio-based Michael acceptor and demonstrates that the reaction order can be altered by the choice of catalyst, solvent, or the concentration of the amine reactant. Optimized protocols can suppress the isomerization of dimethyl itaconate into unreactive regioisomers.
Article
Chemistry, Applied
Fushuai Li, Zhihong Yang, Yanyan Yang, Qiuhong Huang, Xuling Chen, Pengfei Li, Mingxin Dong, Wenjun Li
Summary: A chiral phosphorus acid catalyzed enantioselective 1,4-conjugate addition of arylamines to in situ formed 7-methylene-7H-indoles from 7-indolylmethanols has been successfully developed for the first time without the use of additives. The catalytic protocol enables the formation of 1,4-adducts with a nitrogen-containing tertiary carbon stereocenter in moderate to high yields and good enantioselectivity under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Pritam Roy, Anugam V. Krishna, Dhevalapally B. Ramachary
Summary: Biologically important 4-alkylsyncarpic acids were synthesized through a one-pot organocatalytic reaction, and their synthetic applications were demonstrated. Formal total synthesis of important derivatives was achieved starting from 4-alkylsyncarpic acids. The importance of C-alkylated products was further showcased.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Abhisek Midya, Laxman Devidas Khalse, Prasanta Ghorai
Summary: An unprecedented enantioselective organocatalytic spirocyclization strategy was developed by in situ generation of aminoisobenzofulvenes and utilizing iminium-enamine catalysis for a reductive Michael/aldol-condensation/Michael addition cascade. This strategy showed remarkable success in the synthesis of all carbon quaternary spirocycles and demonstrated post-methodological manipulation of the products.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Andreas Kunzendorf, Mohammad Saifuddin, Gerrit J. Poelarends
Summary: This study reports that tailored variants of the promiscuous enzyme 4-oxalocrotonate tautomerase (4-OT) can accept diverse aliphatic alpha,beta-unsaturated nitroalkenes as substrates for acetaldehyde addition. Highly enantioenriched aliphatic (R)- and (S)-gamma-nitroaldehydes were obtained in good yields using two enantiocomplementary 4-OT variants. These findings underscore the synthetic potential of 4-OT for the preparation of structurally diverse synthons for bioactive analogues of Pregabalin.
Review
Chemistry, Organic
Pratibha Sharma, Raakhi Gupta, Raj K. Bansal
Summary: The article reviews the literature on asymmetric aza-MR of amines and amides catalyzed by organocatalysts in the past 10 years. Studies show that both types of organocatalysts, whether through non-covalent interactions or through covalent bond formation, play important roles in this reaction.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Gen Liu, Danni Hao, Kai Wang, Gang Dong, Xue Yu, Rui Xu, Mei Ji, Xiaodong Zhu, Yanqing Ma, Lei Ma
Summary: In this study, cetylpyridinium chloride was used as a model molecule to investigate the ring-opening process through in situ SERS technique. The results showed that the surface plasmonic resonance of Au nanoparticles promoted the reaction, suggesting potential applications of SERS in studying high-energy cost reactions in situ.
JOURNAL OF PHYSICAL CHEMISTRY C
(2021)
Article
Chemistry, Physical
Ael Cador, Guillaume Hoffmann, Vincent Tognetti, Laurent Joubert
Summary: This paper investigates the aza-Michael additions, which are key-reactions in organic synthesis, from a theoretical perspective using a representative database of weak, medium, and strong electrophiles. The study focuses on the full mechanism of the reaction, including the creation of the C-N bond and proton transfer, and examines the catalytic role of the amine reagent through a comprehensive sampling of the potential energy surface. The computed activation barriers are then compared with experimental electrophilicity values to understand the factors governing the reaction and provide a unified view of these important chemical processes.
THEORETICAL CHEMISTRY ACCOUNTS
(2022)
Article
Chemistry, Organic
Qijian Ni, Xuyang Wang, Da Zeng, Qianling Wu, Xiaoxiao Song
Summary: By using a chiral bifunctional squaramide catalyst, an asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been achieved, providing an efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
Article
Chemistry, Physical
Sarah G. Pate, Hui Xu, Casey P. O'Brien
Summary: This study developed a new tool to observe the formation of CO2 transport intermediates in amine-based membranes and revealed the influence of water on the CO2 transport mechanism. The results showed that water can enhance CO2 transport by catalyzing the formation of intermediates.
JOURNAL OF MATERIALS CHEMISTRY A
(2022)
Article
Materials Science, Multidisciplinary
Ruiqi Zeng, Nan Wang, Wei Li
Summary: In this study, the effect of MgO addition on the reduction of Hongge vanadium titanomagnetite pellet (HVTMP) was investigated. The results showed that the addition of MgO increased the porosity of HVTMP, leading to a higher initial reduction rate but a lower final reduction degree. X-ray diffraction analysis revealed the formation of MgFe2O4, which hindered the further reduction of Fe2TiO4 and the migration of metallic iron. The reduction swelling decreased and the compressive strength of the reduced HVTMP increased with increasing MgO addition, mainly due to the increased hardness. This study establishes a relationship between MgO and reduction, providing valuable insights for the effective utilization of HVTMP in shaft furnaces and the development of sustainable metallurgy.
Article
Energy & Fuels
Qixiang Kang, Xinghua Zhang, Yanyan Cui, Xuelai Zhao, Wuyu Wang, Jiapeng Zhang, Qi Zhang, Longlong Ma
Summary: Cycloalkanes jet fuel derived from biomass is the perfect alternative to fossil fuel. The Mannich-Michael reaction of cyclopentanone and formaldehyde followed by hydrodeoxygenation (HDO) is a promising method for producing high-density jet fuel. The combination of pyrrolidine and acetic acid showed high catalytic activity in the one-pot Mannich-Michael reaction under mild conditions. By using the enamine catalytic pathway, a high yield of condensed products and conversion of cyclopentanone was achieved. The alkali-treated H beta 25-1 catalyst combined with Pd/C effectively catalyzed the hydrodeoxygenation of the condensed products, resulting in a high yield of dicyclopentylmethane with desirable density and heating value. This work provides a new route for producing high-density jet fuel from lignocellulosic compounds.
Article
Chemistry, Organic
Lorenzo Serusi, Laura Palombi, Giovanni Pierri, Antonia Di Mola, Antonio Massa
Summary: The asymmetric synthesis of novel 3-substitued isoindolinones was achieved using the asymmetric nitro-Mannich reaction and the in situ cyclization reaction. High enantioselectivities and yields were obtained in the presence of a neutral bifunctional organocatalyst. The investigation of the reactivity of the obtained products also revealed the potential for further functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fatima Rammal, Annie-Claude Gaumont, Sami Lakhdar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jingjing Zhang, Quan Chen, Robert J. Mayer, Jin-Dong Yang, Armin R. Ofial, Jin-Pei Cheng, Herbert Mayr
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Zhen Li, Robert J. Mayer, Armin R. Ofial, Herbert Mayr
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Alya Inial, Fabrice Morlet-Savary, Jacques Lalevee, Annie-Claude Gaumont, Sami Lakhdar
Article
Chemistry, Organic
Fatima Rammal, Di Gao, Sondes Boujnah, Annie Claude Gaumont, Aqeel A. Hussein, Sami Lakhdar
Article
Chemistry, Physical
William Lecroq, Jules Schleinitz, Mallaury Billoue, Anna Perfetto, Annie-Claude Gaumont, Jacques Lalevee, Ilaria Ciofini, Laurence Grimaud, Sami Lakhdar
Summary: An unprecedented combination of light and P(III)/P(V) redox cycling was utilized for efficient deoxygenation of aromatic amine N-oxides. Additionally, it was found that a wide range of aliphatic amine N-oxides could be deoxygenated simply by using phenylsilane. These methods, operating under metal-free conditions, demonstrated good tolerance to various functionalities and high chemoselectivity.
Article
Chemistry, Organic
Manfred Hartnagel, Armin R. Ofial, Herbert Mayr
SYNTHESIS-STUTTGART
(2023)
Article
Multidisciplinary Sciences
Timothee Constantin, Bartosz Gorski, Michael J. Tilby, Saloua Chelli, Fabio Julia, Josep Llaveria, Kevin J. Gillen, Hendrik Zipse, Sami Lakhdar, Daniele Leonori
Summary: This work presents a distinct reactivity mode enabled by quantum mechanical tunneling using a cyclohexadiene derivative as the abstractor under mild photochemical conditions. Experimental and computational studies reveal a noncanonical pathway for activation of various organic compounds.
Article
Chemistry, Organic
Solene Morand, William Lecroq, Philippe Jubault, Sami Lakhdar, Jean-Philippe Bouillon, Samuel Couve-Bonnaire
Summary: Gem-bromofluoroalkenes were reacted with phosphite under irradiation using Fukuzumi's catalyst, resulting in the synthesis of valuable stable mimics of phosphates, gem-fluorophosphonate derivatives. The reaction exhibited good to excellent yields and excellent chemical tolerance.
Article
Chemistry, Organic
Valentin Magne, Corentin Bellanger, Aqeel A. A. Hussein, Nathalie Saffon-Merceron, Sami Lakhdar
Summary: This article presents a metal-free synthesis method for aryltriphenylgermanes, which involves the reaction of triphenylgermane with fluoro(hetero)arenes under blue light irradiation in the presence of a base. The reaction proceeds under mild conditions and exhibits tolerance towards a few functionalities. The scope and limitations of this novel approach are analyzed based on preliminary mechanistic studies.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Valentin Quint, Thi Hong Van Nguyen, Gary Mathieu, Saloua Chelli, Martin Breugst, Jean-Francois Lohier, Annie-Claude Gaumont, Sami Lakhdar
Summary: Regioselective phosphonation of pyridines can be achieved through activation of the pyridine ring with a Lewis acid to enable nucleophilic addition of a phosphine oxide anion, followed by oxidation with an organic oxidant. This method provides access to various 4-phosphonated pyridines with good to excellent yields. In addition, C2-phosphonated pyridines can be synthesized using strong Lewis basic phosphorus nucleophiles or strong Lewis acidic pyridines in certain cases. The mechanistic investigations help understand the factors controlling the reactivity and selectivity of this reaction.
ACS ORGANIC & INORGANIC AU
(2023)
Article
Chemistry, Organic
Hend Besrour, Matthieu Hedouin, Lina Truong, Sami Lakhdar, Hassan Oulyadi
Summary: In this study, the interaction between a diphenyliodonium salt and trivalent phosphorus compounds was investigated using {H-1, F-19, P-31} NMR and DFT calculations. The importance of blue light in the reaction was highlighted, and the formation of a phosphonium intermediate was identified. The formation of an EDA complex was characterized, and the significance of acetonitrile for the formation of this complex was demonstrated. The study was further extended to other phosphonium salt formation reactions, and the stability and photoreactivity of the complexes were investigated using DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Saif Eddine Cherif, Avisek Ghosh, Saloua Chelli, Isabelle M. Dixon, Jamil Kraiem, Sami Lakhdar
Summary: This work demonstrates a novel approach to obtain the thermodynamically unfavorable Z-isomer in olefin cross-metathesis reactions by combining a classical E-selective catalyst with a readily available photocatalyst. The scope and limitations of this approach are discussed based on computational and experimental mechanistic data.
Article
Chemistry, Multidisciplinary
Batoul Rkein, Maxime Manneveau, Ludovik Noel-Duchesneau, Karine Pasturaud, Muriel Durandetti, Julien Legros, Sami Lakhdar, Isabelle Chataigner
Summary: The electrophilicity of 4 different 3-nitroindole derivatives has been evaluated, showing unexpected values for aromatic compounds. It was found that 3-nitroindoles can react smoothly with Danishefsky's diene at room temperature, yielding (4+2) cycloadducts in good yields.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Fatima Rammal, Di Gao, Sondes Boujnah, Aqeel A. Hussein, Jacques Lalevee, Annie-Claude Gaumont, Fabrice Morlet-Savary, Sami Lakhdar
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)
