Article
Chemistry, Multidisciplinary
Shengjie Jiang, Yanping Cai, Thayalan Rajeshkumar, Iker del Rosal, Laurent Maron, Xin Xu
Summary: This work presents the synthesis, characterization, and reactivity of the first well-defined zinc α-diazoalkyl complex. The complex reacts with a nickel catalyst to form an α-zincated phosphorus ylide, or undergoes [3+2] cycloaddition with CO2 or CO to produce a five-membered heterocyclic product. The use of CO in the cycloaddition reaction is unprecedented, demonstrating a novel CO reaction mode.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Siyuan Wang, Yuqiao Zhou, Wanlong Xiao, Zegong Li, Xiaohua Liu, Xiaoming Feng
Summary: In this study, the enantioselective synthesis of complex tricyclo[3.2.2.0]nonenes through the Diels-Alder reaction was reported. Racemic norcaradienes prepared from the visible-light-mediated dearomative cyclopropanation of m-xylene were utilized as dienes, and enone derivatives were used as dienophiles. The presence of a chiral cobalt(ii) complex of chiral N,N'-dioxide allowed for a kinetic asymmetric transformation with high diastereo- and enantioselectivity in most cycloaddition processes.
Article
Chemistry, Multidisciplinary
Sudeshna Mondal, Chandan Kumar Giri, Mahiuddin Baidya
Summary: The weakly coordinating enaminone functionality is essential for the ruthenium-catalyzed C-H bond activation strategy, enabling the regioselective coupling of arenes with diazonaphthoquinones to produce polycyclic benzocoumarins in high yields. The protocol operates through a Ru(II)/Ru(IV) catalytic pathway and allows for the diversification of various pharmacophore-coupled substrates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yangjinxiu Zhou, Tengfei Pang, Yu Liu, Fangrui Zhong, Guojiao Wu
Summary: We present a highly intriguing and underexplored multi-component reaction involving diazo molecules for polyene formation. This reaction involves coupling of 2,2,2-trifluorodiazoethane and aryl alkynes mediated by iodine under visible light. The reaction provides a straightforward and step-economic access to bistrifluoromethylated 1,3,5-trienes in high stereoselectivity by creating three C=C bonds in a single step under mild conditions.
Article
Chemistry, Organic
Yu-Ting Tian, Fa-Guang Zhang, Jun-An Ma
Summary: A novel Et3N-catalyzed [3 + 2] cycloaddition reaction has been developed for the synthesis of various pyrazoles from allenoates by reacting with acceptor diazo compounds. 3-Alkynoates can also participate in the reaction by isomerizing to allenoates in situ.
Article
Chemistry, Applied
Michal Domanski, Jonas Zurauskas, Joshua P. Barham
Summary: A continuous flow auto-frequency tuning single-mode microwave reactor is presented as a powerful platform for synthesizing alkyl imidazolium salts as ionic liquids/ionic liquid precursors. The reactor achieves near-quantitative yields, high productivities, and record space-time yields, and addresses challenges such as viscosity changes, dielectric property changes, and phase separations.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Review
Chemistry, Inorganic & Nuclear
Md. Gulzar Ahmad, Kaushik Chanda
Summary: The dramatic rise in population has led to an increased demand for raw materials and energy assets, but these resources cannot be easily provided in the same shares. Ionic liquid-supported metal catalysts have demonstrated excellent performance in organic synthesis and are more efficient, environmentally friendly, cost-effective, and reusable compared to other types of metal catalysts.
COORDINATION CHEMISTRY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Yong-Liang Su, Kuiyong Dong, Haifeng Zheng, Michael P. Doyle
Summary: A new catalytic methodology for synthesizing pyrazolines from alpha-diazo compounds and conjugated alkenes was reported. The regiocontrolled addition of diazomethyl radicals to carbon-carbon double bonds followed by intramolecular ring closure and tautomerization achieved a diverse set of pyrazolines in good yields with excellent regioselectivity. This strategy overcomes the limitations of electron-deficient alkenes and opens new opportunities for versatile transformations of diazo compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Bastiaan Kooij, Paul Varava, Farzaneh Fadaei-Tirani, Rosario Scopelliti, Dimitrios A. Pantazis, Gerard P. Van Trieste, David C. Powers, Kay Severin
Summary: In this study, we report the structural characterization of copper complexes with both bridging and terminal alkenylidene ligands. The complexes were obtained by irradiation of Cu-I complexes with N-heterocyclic diazoolefin ligands. The isolation and structural characterization of the complex with a terminal alkenylidene ligand were achieved through crystalline matrix isolation and in crystallo photolysis at low temperature.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xinyu Zhang, Jinli Zhang, Jie Chen, Banghua Zhou, Jian Zhang, Shunhong Chen, Jian Wu, Yaojia Jiang
Summary: An efficient and straightforward synthetic method for constructing trifluoromethyl 2H-thiophenes through [4 + 1] cycloaddition of enaminothiones with trifluoromethyl N-tosylhydrazones has been disclosed. The cycloaddition platforms were found to be compatible with a broad substrate scope and to show high regio- and stereo-selectivities under very mild reaction conditions such as room temperature, neutral media and low loading of catalyst.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ricardo Labes, Julio C. Pastre, Richard J. Ingham, Claudio Battilocchio, Henrique M. Marcon, Mariana C. F. C. B. Damiao, Duc N. Tran, Steven V. Ley
Summary: This study reports the rapid synthesis of 2-pyrazolines from aldehydes via [3 + 2] cycloaddition of unstabilised diazo species and mono and di-substituted alkenes. The development includes semi-continuous and fully continuous methods, with a fully automated compound library generation and a graphical interface for automation control.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Organic
Sourav Roy, Apurba Biswas, Hrishikesh Paul, S. k Ariyan, Indranil Chatterjee
Summary: A rare example of visible-light-mediated diverse reactivity of N-sulfinylamines with different types of carbene precursors has been discovered. This method allows for the synthesis of valuable amides and alpha-iminoesters, without the use of transition metals or coupling reagents, by utilizing acylsilanes, aryldiazoacetates, and diazocarbonyls as carbene precursors. The use of visible light as a key promoter makes this method easily accessible.
Article
Chemistry, Organic
Estefania M. Martinis, Alejandro Montellano, Andrea Sartorel, Mauro Carraro, Maurizio Prato, Marcella Bonchio
Summary: The study examined the cycloaddition of azomethine ylides to C-60 in o-DCB, evaluating the impact of an IL additive and the boosting effect of MW-induced dielectric heating. The IL additive plays a dual role in stabilizing the ylide intermediate and promoting retro-cycloaddition at high temperatures. The experiments showed a preference for the selective formation of trans bis-fulleropyrrolidine regioisomers under the conditions explored, consistent with DFT computational analysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nicholas J. Porter, Emma Danelius, Tamir Gonen, Frances H. Arnold
Summary: This study developed a catalyst that uses diazirines as carbene precursors, providing a new strategy for selective carbene transfer. By engineering variants of ApePgb protoglobin, selective carbene transfer from diazirines can be achieved at room temperature. The structure of an ApePgb variant, determined by microcrystal electron diffraction, revealed how evolution has enhanced access to the heme active site for this new-to-nature catalysis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yana D. Petri, Clair S. Gutierrez, Ronald T. Raines
Summary: Chemical tools for on-demand protein activation have been expanded to solvent-accessible carboxyl groups using the preferential reactivity of diazo compounds. The hydrolytic activity of caged lysozyme on bacterial cell walls was restored with small-molecule triggers, demonstrating the potential broad applicability of this simple chemical strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Analytical
Sonaimuthu Mohandoss, Hari Datta Khanal, Subramanian Palanisamy, SangGuan You, Jae-Jin Shim, Yong Rok Lee
Summary: A new photoluminescent probe based on multiple heteroatom co-doped carbon dots has been synthesized for ratiometric detection of Hg2+ ions. The probe exhibits good aqueous solubility, stability, and high quantum yield, and shows high selectivity and sensitivity towards Hg2+ ions.
ANALYTICAL METHODS
(2022)
Article
Chemistry, Multidisciplinary
Shreedhar Devkota, Sonaimuthu Mohandoss, Yong Rok Lee
Summary: An efficient and facile In(iii)-catalyzed reaction of 3-diazoindolin-2-ones with different arylhydrazines is demonstrated, providing a rapid synthetic route to diversely functionalized 3-arylhydrazonoindolin-2-ones in good yields. This novel method introduces biologically and photo-functionally interesting hydrazones at the 3-position of indolin-2-ones.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Sana Jamshaid, Yong Rok Lee
Summary: A novel, facile, and efficient Lewis-acid-catalyzed [4 + 1] annulation protocol has been developed for the construction of functionalized polycyclic-fused furans. This methodology provides a rapid synthetic route to divergently orientated polycyclic furans in good yields, without the need for transition metals and ligands. Additionally, this protocol can be used to synthesize multisubstituted furans.
Article
Chemistry, Organic
Sagar D. Nale, Hari Datta Khanal, Yong Rok Lee
Summary: A palladium-catalyzed desulfitative coupling of quinoxalin-2(1H)-ones with arylsulfonyl chlorides is demonstrated. The reaction allows for the synthesis of C3-arylquinoxalin-2(1H)-ones. The method enables successful coupling of chloro- and fluoro-aryl sulfonyl chlorides with quinoxalin-2(1H)-ones without carbon-halogen bond cleavage.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Raju S. Thombal, Peter Yuosef M. Rubio, Daesung Lee, Debabrata Maiti, Yong Rok Lee
Summary: Metal catalyzed cascade C-H activation/annulation is a highly promising approach for the construction of aromatic and heteroaromatic compounds. Pd-complexes play a crucial role in this method, enabling high catalytic efficiency through the activation of molecules bearing a directing group.
Article
Environmental Sciences
Ramaraj Sukanya, Sonaimuthu Mohandoss, Yong Rok Lee
Summary: This paper presents a one-pot hydrothermal synthesis method to prepare Mo-doped MnWO4 NCs for the electrochemical detection of NTZ. The introduction of defect engineering on metal tungstates shows promising potential in developing high-performance sensing materials for drug molecules.
Article
Chemistry, Applied
Shreedhar Devkota, Muhammad Saeed Akhtar, Yong Rok Lee
Summary: This study explores the rhodium(III)-catalyzed sp(2)/sp(3) C-H activation/annulation of 2-arylquinazolin-4(3H)-ones with 3-methylmaleimides. Diversely functionalized isoindoloquinazolinones were obtained in good yields upon reaction with various maleimides. This Rh(III)-catalyzed protocol can be applied for the chemo- and diastereoselective synthesis of various polyheterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Perumal Muthuraja, Muhammad Saeed Akhtar, Purushothaman Gopinath, Yong Rok Lee
Summary: A substrate-controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)-catalyzed C-H bond activation is developed, providing diversely functionalized indanonylpyrroline-2,5-dione derivatives and biologically intriguing spiroindanonylpyrroline-2,5-diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Eswaran Kamaraj, Prasanta Roy, Yong Rok Lee
Summary: A rhodium-catalyzed [5+1] cycloaddition through C-H activation/O-annulation strategy is described for synthesizing biologically interesting isochromenes. This method selectively provides divergently functionalized isochromenes containing spirosuccinimide and maleimide scaffolds based on the maleimides and itaconimides used as substrates. It demonstrates a broad substrate scope, remarkable functional group tolerance, and high regioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Hari Datta Khanal, Karuna Mahato, Yong Rok Lee
Summary: An effective and unprecedented In(III)-catalyzed benzannulation of 3-formyl-4-pyrones with simple arylacetylenes is reported, which enables their conversion into structurally diverse salicylaldehyde-bearing ortho-terphenyl frameworks. This transformation is achieved via an In(III)-catalyzed C-O bond extrusion and proceeds without the requirement for an external oxidant. The synthetic utility of this protocol is demonstrated by the transformation of the obtained product into molecules with bisindole, chromene, and oxime moieties.
Article
Chemistry, Multidisciplinary
Esakkimuthu Shanmugasundaram, Vigneshkumar Ganesan, Vimalasruthi Narayanan, Kannan Vellaisamy, Rajaram Rajamohan, Yong Rok Lee, Selvam Kaliyamoorthy, Stalin Thambusamy
Summary: Carbon quantum dots (CQDs) have exceptional optical and electrical qualities, making them important for various applications. Heteroatom-doped CQDs, such as B-CQDs, N-CQDs, and F-CQDs, were synthesized and their bandgap characteristics, absorption patterns, and emission characteristics were examined. Photoactive films were created by electropolymerizing PANI into the CQDs, and their photophysical and electronic characteristics were analyzed. The PANI-N-CQD film showed great potential as a photoactive material for organic solar cell applications.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Organic
Hari Datta Khanal, Muthuraja Perumal, Yong Rok Lee
Summary: The reduction of the stable nitro group is a fundamental and widely used transformation for the construction of complex and functionalized heterocyclic architectures. The reactivity of the nitro group in the 2-nitrostyrene moiety not only triggers the formation of carbon-nitrogen bonds, but also offers the opportunity for annulation and heteroannulation, providing a cascade process for the synthesis of highly conjugated natural and unnatural molecules. This review comprehensively discusses the use of 2-nitrostyrene motifs in the synthesis of various N-heterocycles, highlighting their important features, reactivities, and mechanisms.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Eun Hee Cho, Muhammad Saeed Akhtar, Mohammad Aslam, Raju S. Thombal, Xin Li, Jae-Jin Shim, Yong Rok Lee
Summary: The selective activation of carbazoles and indolines via transition metal-catalyzed reactions allows for the rapid installation of succinimide groups at specific positions, demonstrating the intrinsic reactivity of indolines and mild reaction conditions to generate succinimide-substituted indoles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Ei Seul Yun, Muhammad Saeed Akhtar, Sonaimuthu Mohandoss, Yong Rok Lee
Summary: A catalyst-free microwave-assisted annulation protocol has been developed for the preparation of biologically interesting pyrido-fused quinazolinones and pyrido[1,2-a]benzimidazoles. This approach offers a rapid and facile method with a broad substrate scope, good yields, catalyst-free conditions, and high functional group tolerance. The synthesized compound can also serve as an on-off photoluminescent probe for the selective detection of Fe3+ and Ag+ metal ions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Raju S. Thombal, Mohammad Aslam, Sonaimuthu Mohandoss, Yong Rok Lee
Summary: This study describes a Rh(III)-catalyzed C-H activation reaction of acetanilides with beta-hydroxy substituents and alkynes, leading to the formation of O-acylated N-H indole compounds. This method is highly regioselective for unsymmetrical alkynes and can be used with various types of compounds, including chiral beta-hydroxy compounds. The reaction has several advantages, including cascade bond formation, low catalyst loading, 100% atom economy, and high regioselectivity. Additionally, the indole compounds formed in this reaction can be used as fluorescent probes for the selective sensing of Fe3+ ions.
NEW JOURNAL OF CHEMISTRY
(2022)
