Article
Chemistry, Organic
Yanfeng Gao, Hui Wang, Xiaoquan Chen, Yiyang Qiao, Zhiwei Miao
Summary: We present a highly efficient and diastereoselective gold and palladium sequential relay catalysis system for the synthesis of furan-fused eight-membered heterocycles. By utilizing a one-pot procedure, readily available enynamides undergo cyclization to generate azadienes in situ, which then engage in diastereoselective formal[4 + 4] cycloadditions with gamma-methylene-delta-valerolactones. This method enables the rapid and efficient construction of a range of furan-fused azacyclooctanes with diverse substituents in good yields (63-97%) and a high level of diastereoselectivity (7:1 → 20:1 dr).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Enrico Marcantonio, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, Franca Zanardi
Summary: The remote enolization strategy, strategic exploitation of noncovalent bifunctional organocatalysis, and efficient stereoselective trapping of dienolate intermediates with nitroolefins led to the successful synthesis of functionalized, chiral carbocycle-fused uracils with three contiguous stereocenters in one step, showing good levels of enantioselectivity and complete diastereocontrol. Furthermore, the enantiopure products could be obtained via simple one-cycle recrystallizations and the scaffolds could be further functionalized without losing their chiral integrity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Paul Teixeira, Stephanie Bastin, Vincent Cesar
Summary: N-heterocyclic carbene (NHC) ligands have gained considerable importance in gold catalysis due to their appealing properties. Fused polyaromatic NHCs, featuring fused aromatic rings, have attracted wider attention in recent years for their unique structural and electronic properties. These versatile platforms offer superior activity and/or selectivity in NHC-gold catalysis and provide opportunities for further functionalization, chirality introduction, stimuli-responsiveness, or cooperativity within the NHC-gold systems.
ISRAEL JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Pragati Shukla, Madan D. Ambhore, Venkataramanarao G. Anand
Summary: The electronic properties of a hexaphyrin were fine-tuned by core-modification, resulting in a Huckel aromatic 30 pi hexaphyrin with two pyrrole and four furan rings in the pi-conjugated pathway. This Huckel aromatic hexaphyrin changed its conformation upon two-electron ring oxidation with triflic acid or Meerwein salt [Et3O](+)[SbCl6](-), forming 28 pi Mobius aromatic dication species. The reversible aromatic transition was confirmed through spectroscopic techniques and quantum chemical calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Weinan Chen, Si Liu, Yingjian Ren, Shoudong Xie, Chuan Yan, Zhanglang Zhou, Gang Zhou
Summary: Three S-fused PAHs with cyclopenta[b]thiopyran moieties were successfully synthesized and showed significant halochromic properties. The longest PAH exhibited absorption onset at 1110 nm and was selectively protonated by stronger acid. The non-emissive S-fused PAHs showed strong fluorescence after protonation, which violated the Kasha's rule.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sebastian Mummel, Felix Lederle, Eike G. Huebner, Jan C. Namyslo, Martin Nieger, Andreas Schmidt
Summary: Sydnone methides are rare compounds that can form pi-electron rich anionic N-heterocyclic carbenes and coordinate with various metals, while also undergoing C-C coupling reactions under specific catalysts. Studies have determined their electronic properties and NMR spectra.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jinhang Yu, Mengjiao Xu, Xinyuan Wang, Bei Zhang, Hui Mao, Xin Lv, Liejin Zhou
Summary: A novel catalyst-controlled reaction is reported, which allows for the rapid and efficient synthesis of a series of bicyclic compounds by using readily available acyclic enyne-amides and crotonate-derived sulfur ylides as substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Yang Liu, Daguan Xie, Yutao Rao, Ling Xu, Mingbo Zhou, Atsuhiro Osuka, Jianxin Song
Summary: In this study, directly fused porphyrinoids with cycloheptatriene linkage were synthesized through chemical reactions. These fused hybrids exhibit unique structures and properties, which were fully characterized using X-ray structural analysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, Hiroaki Ohno
Summary: This study demonstrates the successful synthesis of benzannulated indole-fused medium-sized tetracycles through alpha-imino gold carbene chemistry, providing a new approach to explore bioactive compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Inorganic & Nuclear
Olaya Bernardo, Silvia Gonzalez-Pelayo, Luis A. Lopez
Summary: The marriage of heterocyclic compounds with ferrocene has been a fruitful field of research, with several ferrocene-embedded heterocyclic compounds reported in recent years. The synergistic combination of properties from both heterocyclic and metallacyclic motifs in fused systems has led to interesting applications, particularly in asymmetric catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Evgeny B. Ulyankin, Anastasia S. Kostyuchenko, Sergey A. Chernenko, Mikhail O. Bystrushkin, Anna L. Samsonenko, Anton L. Shatsauskas, Alexander S. Fisyuk
Summary: A new approach based on iodine-promoted photocyclization was developed for the synthesis of fused benzothiophene derivatives, providing an efficient method compared to traditional oxidative coupling and palladium-catalyzed intramolecular arylation. This method allows for the synthesis of a variety of functionally substituted fused heterocycles containing pyridine and carbazole moieties.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Stefan M. Marschner, Ritesh Haldar, Olaf Fuhr, Christof Woell, Stefan Braese
Summary: This study reported the successful synthesis of a series of 5,15-bis(4-ethoxycarbonylphenyl)porphyrin derivatives through Suzuki and Sonogashira cross-coupling reactions, fully characterized and systematically investigated for their suitability in synthesizing surface-anchored MOF thin films.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Henric Steffenfauseweh, Yury V. Vishnevskiy, Beate Neumann, Hans-Georg Stammler, Diego M. Andrada, Rajendra S. Ghadwal
Summary: In this study, the synthesis, characterization, and reactivity of the first cyclic C2As2-diradicaloid compound were reported. The compound exhibits a planar C2As2 ring, is diamagnetic, and shows well resolved NMR signals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Binbin Ming, Chuan Yan, Shoudong Xie, Si Liu, Yingjian Ren, Hao Zong, Weinan Chen, Gang Zhou
Summary: In this study, a series of thiepine-containing polycyclic S-heterocycles were synthesized via different methods, improving the thermal stability of the thiepine derivatives. Nucleus-independent chemical shift calculations revealed aromatic and nonaromatic characteristics of the incorporated thiopyran and thiepine rings, respectively. The findings provide a facile synthetic methodology for S-fused multi-membered polycyclic heterocycles and a novel construction strategy for thermally stable thiepine derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rajasekar Reddy Annapureddy, Christian Jandl, Thorsten Bach
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Kai Wu, Liang-Liang Wu, Cong-Ying Zhou, Chi-Ming Che
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Hai-Xu Wang, Kai Wu, Chi-Ming Che
Summary: This paper summarizes recent research on metal-quinoid carbene chemistry, focusing on dirhodium-catalyzed C(sp(2))-H insertion reactions, isolation and characterization of Ruthenium(II) porphyrin QC complexes, and iridium(III) porphyrin-catalyzed C(sp(3))-H insertion reactions.
Article
Chemistry, Multidisciplinary
Rajasekar Reddy Annapureddy, Finn Burg, Johannes Gramueller, Tino P. Golub, Christian Merten, Stefan M. Huber, Thorsten Bach
Summary: An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source and a silver-based catalyst system, producing 21 chiral sulfimides in high yields and with significant enantiomeric excess. The reaction demonstrates high site-selectivity and potential for kinetic resolution of chiral sulfoxides. Mechanistic evidence supports the involvement of a heteroleptic silver complex in the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Johannes H. Harenberg, Niels Weidmann, Alexander J. Wiegand, Carla A. Hoefer, Rajasekar Reddy Annapureddy, Paul Knochel
Summary: The study demonstrates a novel method for the on-demand generation of (2-ethylhexyl)sodium from 3-(chloromethyl)heptane using a sodium-packed-bed reactor under continuous flow conditions, producing a solution free of elemental sodium suitable for various synthetic applications. The new procedure eliminates the need for storing alkylsodium and minimizes the handling of metallic sodium, enhancing safety in laboratory experiments. The (2-ethylhexyl)sodium reagent proves to be highly versatile, allowing for in-line Br/Na-exchanges and directed sodiations with subsequent trapping of arylsodium intermediates with various electrophiles in batch reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xue-Yun Shang, Hua-Ying An, Ting Zhang, Jin-Hong Lin, Fei Hao, Dong-Hai Yu, Ji-Chang Xiao, Tian-Duo Li
Summary: This study quantitatively described the affinity of fourteen metal ions and two representative ligands using density functional theory, and explored different methods to understand the evolution of affinity.
CHEMICAL PHYSICS LETTERS
(2021)
Article
Chemistry, Applied
Yong Li, Yan Li, Tao Chen, Xiaodeng Yang, Congde Qiao, Fei Hao, Mingxia Liu
Summary: This paper investigates the effect of crystallized calcium carbonate particles (cry-CaCO3) on the properties of HTCC/CMC films. The results show that cry-CaCO3 particles promote the homogeneous distribution of the HTCC/CMC matrix, significantly improving mechanical properties while having little effect on thermal stability, whiteness, and wettability of the films. The study further characterizes the cry-CaCO3 particles and reveals that the strong electrostatic, hydrogen bonding, and flexible interaction between CMC and cry-CaCO3 particles play a key role in improving the mechanical properties of HTCC/CMC films.
CARBOHYDRATE POLYMERS
(2022)
Article
Chemistry, Organic
Fang Xiao, Jin-Hong Lin, Fei Hao, Xing Zheng, Yu Guo, Ji-Chang Xiao
Summary: A protocol for visible light mediated C-H trifluoromethylation of unactivated (hetero)arenes under blue LED irradiation has been developed. It enables the rapid construction of a range of CF3-containing (hetero)arenes in moderate to high yields from the readily accessible trifluoromethylsulfonyl-pyridinium salt (TFSP). This protocol is also suitable for nitrogen-containing aromatic heterocycles, which are potentially useful in medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Johannes H. Harenberg, Rajasekar Reddy Annapureddy, Konstantin Karaghiosoff, Paul Knochel
Summary: This study reports a lateral sodiation reaction for alkyl(hetero)arenes using a hexane-soluble sodium compound generated on demand, in the presence of TMEDA. The reaction can be conducted under batch and continuous flow conditions. The resulting benzylic sodium species can react with various electrophiles. This method has great potential for synthetic applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Jiang-Pin Tan, Jin-Hong Lin, Fei Hao, Ji-Chang Xiao
Summary: A protocol is described for the heptafluoroisopropylthiolation of benzyl halides using a HFP/CsF/S-8 system, enabling the rapid synthesis of (CF3)2CFS-containing compounds. This method shows potential for the synthesis of biologically active molecules.
JOURNAL OF FLUORINE CHEMISTRY
(2022)
Article
Chemistry, Organic
Fei Hao, Tian Zhang, Donghai Yu, Xiaodeng Yang, Hua-Wei Jiang, Ji-Chang Xiao, Qing-Yun Chen
Summary: A novel porphyrin analogue with a C C bond incorporated into an 18-pi-conjugated system, named Tetraphenylporphyriyne (Pynel), has been synthesized via cleavage of the N-confused pyrrolic ring in Ag(III) N-confused tetraphenylporphyrin. The structure of Pynel was confirmed using various spectroscopic techniques, and the mechanism of the cleavage process was investigated using theoretical calculations. The successful synthesis of other Pynes demonstrated the generality of this methodology.
Article
Chemistry, Medicinal
Kailash Singh, Shaik Abdullah Nawabjan, Li Zhang, Hani El-Nezami, Rajasekar Reddy Annapureddy, Billy KC. Chow
Summary: Recent studies have identified a small compound-based Secretin receptor modulator with potential anti-hypertensive effects through structure based drug design strategy. The modulator has shown similar blood pressure lowering effect as SCT peptide, with a longer half-life and oral bioavailability.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kai Wu, Xuyang Zhang, Liang-Liang Wu, Jie-Sheng Huang, Chi-Ming Che
Summary: In this study, we reported a modular approach to the synthesis of trifluoromethyl-bearing 5-membered rings through direct rhodium-catalyzed carbene insertion into C(sp(3))-H bonds. The reaction showed good control over site- and stereochemistry, and was applicable for the synthesis of chiral CF3 analogues. Stoichiometric reactions of ruthenium carbene complexes provided evidence for the involvement of metal carbene species in the catalytic cycle. DFT calculations explained the origin of selectivity in the benzylic C-H insertion reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Multidisciplinary
Fei Hao, Hailan Wang, Donghai Yu, Zhenwei Liu, Tiantian Zhang, Mingyao Shen, Tao Yu
Summary: Near-infrared mechanoluminescence materials have great potential in higher order encryption and biomechanical visualization in vivo. This study reports the design, synthesis, and photophysical studies of the first organic host/guest (H/G) NIR mechanoluminescence system. The system exhibits pure NIR mechanophosphorescence that is invisible to the naked-eye and has potential applications in higher order encryption and biomechanical visualization.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Fei Hao, Xueyun Shang, Zhenwei Liu, He Zhang, Jin-Hong Lin, Ji-Chang Xiao
Summary: A Rh-catalyzed tunable defluorinative borylation method was developed to provide high Z/E selectivities for allylborylated monofluoroalkenes or homoallylborylated monofluoroalkenes. Different reaction paths were observed with slight changes in reaction conditions, and the allylborylated monofluoroalkenes could be further converted into dihydroxyl-containing monofluoroalkenes.
CHEMICAL COMMUNICATIONS
(2021)
