Article
Chemistry, Multidisciplinary
Kyoka Sakamoto, Yuki Nagashima, Chao Wang, Kazunori Miyamoto, Ken Tanaka, Masanobu Uchiyama
Summary: The study developed a method for stannylation reactions of terminal alkynes and fluoroarenes, where stannyl anions are photoexcited to form excited triplet stannyl diradical species, showing distinct reactivity and selectivity. This methodology is straightforward, has wide functional group tolerance, high yield, and does not require any catalyst.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Veronique Colovray-Gotteland, Daniel F. Harvey, Barry M. Johnson, Christopher S. Ung, K. Peter C. Vollhardt
Summary: The article discusses the reaction products of 1,7-octadiyne with acetone under specific conditions, as well as the exploration of the reaction scope, demonstrating the different behaviors of different substrates in the reaction process.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Xuan-Xuan Zhao, Tibor Szilvasi, Franziska Hanusch, John A. Kelly, Shiori Fujimori, Shigeyoshi Inoue
Summary: The germanium iron carbonyl complex and the tin iron carbonyl complex were prepared and showed reversible formation of bis(tetrylene) and tetrylene-tetrylone character. Computational analysis further explained the reduction pathway from the chlorotetrylenes to the corresponding complexes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Materials Science, Multidisciplinary
F. Hong, P. F. Shan, L. X. Yang, B. B. Yue, P. T. Yang, Z. Y. Liu, J. P. Sun, J. H. Dai, H. Yu, Y. Y. Yin, X. H. Yu, J. G. Cheng, Z. X. Zhao
Summary: The possible occurrence of superconducting transition in a SnHx sample synthesized under high pressure conditions by laser heating is reported, with an upper critical temperature of about 70 K. This finding provides a new direction for the development of high-temperature superconductors using metallic alloys.
MATERIALS TODAY PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Monika Horvat, Jernej Iskra
Summary: We have developed a cheap, green, mild and environmentally friendly method for the selective cleavage of carbon-carbon double bonds using aqueous hydrogen peroxide and vanadium(V) oxide catalyst. This method converts various compounds into target products with high selectivity, and exhibits better environmental parameters compared to other methods.
Article
Chemistry, Organic
Yajie Yang, Lu Cheng, Mengdan Wang, Liqiang Yin, Ye Feng, Chengyu Wang, Yanzhong Li
Summary: A novel 1,2-difunctionalization of alkynones has been developed via an umpolung strategy for the synthesis of tetrasubstituted olefins. The approach features excellent yields, mild reaction conditions, a broad substrate scope, and operational simplicity.
Article
Chemistry, Organic
Michael D. Delost, Jon T. Njardarson
Summary: We present novel mild approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclo-propanes through Darzens inspired protocols. These anionic annulations, which have been rarely explored previously, yield products with appealing features that make them valuable building blocks for synthesis platforms. Specifically, trisubstituted acetophenone nucleophiles containing SCF3 and bromine substituents in their a position undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Article
Chemistry, Organic
Hongchen Li, Lidong Shan, Lin Min, Yunxiang Weng, Xinyan Wang, Yuefei Hu
Summary: A novel tandem synthesis of 1,3-disubstituted naphthalenes is developed using TfOH-promoted directed-aldol and Friedel-Crafts reactions. The discovery of a chemoselective directed-aldol reaction between different ketones with alpha-hydrogens enables the efficient creation of new C-C bonds and a benzene ring in one pot.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bao-Yin Zhao, Xing-Long Zhang, Rui-Li Guo, Meng-Yue Wang, Ya-Ru Gao, Yong-Qiang Wang
Summary: An efficient strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation, using molecular oxygen as the sole oxidant. The approach has broad substrate scope, good functional group tolerance, and complete E-stereoselectivity, with the reaction mechanism investigated through deuterium-labeling experiments and intermediate experiments.
Article
Chemistry, Organic
Dong-Ting Dai, Jian-Lin Xu, Zhi-Yuan Chen, Zi-Lu Wang, Yun-He Xu
Summary: In this study, chemoselective defluoromethoxylation reactions of 2-trifluoromethyl-1,3-enynes were developed, leading to the selective production of enynic and allenic orthoesters. These products serve as efficient platform molecules for accessing various functionalized allenyl compounds.
Article
Chemistry, Multidisciplinary
Jayaprakash Rao Yerrabelly, Pavan Kumar Bathini, Hemasri Yerrabelly, Kishore Vadapalli
Summary: Ti/Zn-mediated McMurry coupling was used to synthesize a series of unusual CH2-CH2 tethered bis-chromones, showing chemoselectivity towards 4-oxo-4H-chromene-2-carbaldehydes. The study of reaction parameters and reagents further confirmed this selectivity, demonstrating a simple and efficient route for bis-chromone synthesis.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kensuke Suzuki, Naoki Sugihara, Yoshihiro Nishimoto, Makoto Yasuda
Summary: We have achieved the first anti-borylstannylation of alkynes by using (o-phenylenediaminato)borylstannanes. This reaction provides 1-boryl-2-stannylalkenes with excellent regio- and stereoselectivity through a radical mechanism. The mild reaction conditions allow for a wide range of substrates, and the products can be further used in cross- or homocoupling reactions to synthesize important compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Roman Bashkurov, Yosi Kratish, Natalia Fridman, Dmitry Bravo-Zhivotovskii, Yitzhak Apeloig
Summary: Thermolysis of tris(silyl) tin hydride 2 at 70 degrees C for 3 hours leads to the formation of various silyl-stannylene compounds, including the novel octastannacubane 9; the mechanism of this reaction mainly involves elimination reactions and dimerization reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Daniil M. Strashkov, Kirill V. Zavyalov, Pavel A. Sakharov, Anastasiya V. Agafonova, Nikolai V. Rostovskii, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A one-pot synthesis of pyrrolo[1,2-c][1,3]oxazin-1-ones has been achieved through the Rh-2(OAc)(4)-catalyzed annulation reaction of 2-aroyl-substituted NH-pyrroles with diazoesters. The reaction involves the formation of three different products: the annulation product, pyrrolylpyruvate ester, and alpha-(methoxycarbonyloxy)-beta-pyrrol-2-yl cinnamate ester, which are subsequently converted to the pyrroboxazinone derivative in a one-pot process catalyzed by DBU. The reaction mechanism involves four catalytic cycles, including Rh-2(OAc)(4) catalysis and catalysis by the starting pyrrole and the methyl-hemiacetal of the final pyrroboxazinone.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Dean D. Roberts, Mark G. McLaughlin
Summary: The regio- and stereoselective hydrosilylation of various homopropargylic alcohols and their derivatives is discussed, which is tolerant towards different sterically and electronically substituted substrates and yields only the E-vinyl silane as the sole regioisomer. The application of the resulting vinyl silanes in the diastereoselective synthesis of tetrasubstituted oxetanes is demonstrated.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Ayan Das, Benedict J. Elvers, Mithilesh Kumar Nayak, Nicolas Chrysochos, Srinivas Anga, Amar Kumar, D. Krishna Rao, Tharangattu N. Narayanan, Carola Schulzke, Cem B. Yildiz, Anukul Jana
Summary: In this study, we report secondary pyrrolidin-2-ols as a source of cyclic (alkyl)(amino)carbenes (CAAC), which are used to synthesize CAAC-Cu-I complexes and cyclic thiones. This provides a convenient and easy method for the synthesis of CAAC-based Cu-I salts and demonstrates the viability of secondary alcohols as a source of carbenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Avijit Maiti, Benedict J. Elvers, Sachinath Bera, Felix Lindl, Ivo Krummenacher, Prasanta Ghosh, Holger Braunschweig, Cem B. Yildiz, Carola Schulzke, Anukul Jana
Summary: In this study, cyclic(alkyl)(amino)carbenes (CAACs) were found to be one-electron reductants, forming transient radical cations as detected by EPR spectroscopy. The reactivity of the disclosed CAACs was utilized to synthesize a new class of Thiele and Chichibabin hydrocarbons based on acyclic(amino)(aryl)carbene. Additionally, the acyclic(amino)(aryl)carbene-based Chichibabin's hydrocarbon showed a significant population of the triplet state at room temperature.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Ramapada Dolai, Rahul Kumar, Benedict J. Elvers, Pradeep Kumar Pal, Benson Joseph, Rina Sikari, Mithilesh Kumar Nayak, Avijit Maiti, Tejender Singh, Nicolas Chrysochos, Arumugam Jayaraman, Ivo Krummenacher, Jagannath Mondal, U. Deva Priyakumar, Holger Braunschweig, Cem B. Yildiz, Carola Schulzke, Anukul Jana
Summary: A new type of carbodicarbene (CDC) with two different classes of carbenes has been reported, which shows promising potential as organic electron donors and n-dopants. These compounds exhibit notable redox properties and can form carbon-carbon sigma bonds through reactions with [NO][SbF6].
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Hemant Kumar, Maryam Khosraneh, Siva S. M. Bandaru, Carola Schulzke, Silke Leimkuehler
Summary: This study investigates the reversible oxidation of formate to carbon dioxide catalyzed by molybdenum or tungsten-containing formate dehydrogenases. The formation of bicarbonate as the first intermediate during the reaction at the active site is discovered, contrary to previous reports. Bicarbonate formation occurs after an oxygen atom transfer reaction, where the oxygen is transferred from water to formate, followed by a proton-coupled electron transfer or hydride transfer reaction involving the sulfido ligand as the acceptor.
Article
Chemistry, Organic
Subhadip Jana, Benedict J. Elvers, Sebastian Patsch, Pallavi Sarkar, Ivo Krummenacher, Mithilesh Kumar Nayak, Avijit Maiti, Nicolas Chrysochos, Swapan K. Pati, Carola Schulzke, Holger Braunschweig, Cem B. Yildiz, Anukul Jana
Summary: We developed a new method for synthesizing different quinodimethane derivatives by oxidizing bis-N-heterocyclic olefins linked by pi-conjugated aromatic spacers. Stable diimidazolium para- and ortho-quinodimethane derivatives were obtained with para- and ortho-phenylene bridges, as well as with tetrafluoro-p-phenylene and p-anthracene spacers. The influence of imidazolium substituents on the air and moisture stability of the quinodimethane derivatives was emphasized. Different electron transfer processes were observed depending on the pi-conjugated aromatic spacer used, with two one-electron or one two-electron redox transitions between bis-N-heterocyclic olefins and diimidazolium-quinodimethanes. The formation of pi-conjugated radical-cations, which are transient redox intermediates, was confirmed by EPR investigation.
Article
Chemistry, Physical
Muhammad Ikram, Sadia Rehman, Inayat Feroz, Rizwan Khan, Mutasem Omar Sinnokrot, Fazle Subhan, Muhammad Naeem, Carola Schulzke, Carola Schulzke
Summary: A Schiff base ligand (H-NMDP) was synthesized and reacted with Cu2+ to form a copper complex. The crystal structure of Cu-NMDP reveals a coordination polymer with distorted square planar geometry around copper. The copper complex showed higher activity against glioblastoma cells compared to the ligand alone, suggesting its potential application as a chemotherapy agent.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Siva Sankar Murthy Bandaru, Carola Schulzke
Summary: The novel organic salt was synthesized through a Lewis acid and Lewis-base reaction and analyzed by various spectroscopic and crystallographic techniques.
Article
Chemistry, Inorganic & Nuclear
Siva Sankar Murthy Bandaru, Claudia Schindler, Felix Wenzek, Carola Schulzke
Summary: Several synthetic cross-coupling procedures were evaluated for tethering pyrazine to dithiocarbonates. The resulting compounds can serve as pro-ligands and can be converted into ene-dithiolate ligand systems resembling molybdopterin by removing the C=O moiety. The coupling of 2-iodopyrazine with stannylated dithiocarbonate units mediated by copper(I)-thiophene-2-carboxylate in stoichiometric equivalents proved to be the most efficient and reliable method for synthesizing the targeted compounds.
Article
Chemistry, Multidisciplinary
Priyanka Saha, Nicolas Chrysochos, Benedict J. Elvers, Sebastian Paetsch, Sk Imraj Uddin, Ivo Krummenacher, Muneshwar Nandeshwar, Anshika Mishra, Karthik V. Raman, Gopalan Rajaraman, Ganesan Prabusankar, Holger Braunschweig, Prince Ravat, Carola Schulzke, Anukul Jana
Summary: A modular approach for the synthesis of isolable crystalline Schlenk hydrocarbon diradicals from m-phenylene bridged electron-rich bis-triazaalkenes as synthons is demonstrated. The diradical nature and triplet electronic structure of the synthesized compounds are confirmed through EPR spectroscopy and computational analysis. The potential of the modular methodology is further illustrated through the utilization of 4,6-dimethyl-m-phenylene as a coupling unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Martin Napierkowski, Una Janke, Alena Rong, Mihaela Delcea, Siva Sankar M. Bandaru, Carola Schulzke, Patrick J. Bednarski
Summary: In recent years, the biological properties of pentathiepins have gained attention for their potential in cancer treatment. However, their low solubility and stability limitations have hindered biological evaluation. This study investigated the use of liposomes as drug carriers for pentathiepins to improve solubility and stability. The results showed that the aqueous solubility of pentathiepins increased significantly when incorporated into liposomes, and the stability of pentathiepins in the presence of the antioxidant glutathione was enhanced. Moreover, the liposomal loaded pentathiepins demonstrated comparable anticancer activity to free pentathiepins. In conclusion, liposomes are a suitable carrier for pentathiepins and can improve their solubility and stability without compromising their anticancer activity.
ARCHIV DER PHARMAZIE
(2023)
Review
Chemistry, Inorganic & Nuclear
Siva Sankar Murthy Bandaru, Jagrut Shah, Shatrughn Bhilare, Carola Schulzke, Anant R. Kapdi, Julien Roger, Jean-Cyrille Hierso
Summary: This review focuses on the applications of different ferrocenylphosphine ligands in transition metal-catalyzed cross-coupling strategies, including the asymmetric synthesis using chiral ferrocenyl phosphines. It also discusses the latest advances in the chemistry of symmetric achiral di- and polyphosphine ferrocene-based ligands related to metal-catalyzed bond-forming reactions. A cumulative table compiling significant work in this field is provided.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Organic
Jevy V. Correia, Bruno Wilke, Carola Schulzke
Summary: A new alkyne functionalized pterin derivative was successfully synthesized and its purity and chemical structure were confirmed through various methods. The compound can be further modified by utilizing its alkyne moiety and exhibits good solubility in solvents except for water.
Article
Chemistry, Multidisciplinary
Benedict J. Elvers, Sebastian Paetsch, Siva S. M. Bandaru, Vera Krewald, Carola Schulzke, Christian Fischer
Summary: Heteroleptic molybdenum complexes with P2N2 and non-innocent dithiolene ligands were synthesized and electrochemically characterized. The reduction potentials of the complexes were adjusted by ligand-ligand cooperativity via non-covalent interactions. This finding was supported by electrochemical studies, UV/Vis spectroscopy, and temperature-dependent NMR spectroscopy. The observed behavior resembles enzymatic redox modulation through second ligand sphere effects.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Mithilesh Kumar Nayak, Benedict J. Elvers, Debdeep Mandal, Ayan Das, Raghunathan Ramakrishnan, Kaustubh R. Mote, Carola Schulzke, Cem Burak Yildiz, Anukul Jana
Summary: The reduction of 2-H-substituted pyrrolinium cations results in dimerisation or H-abstracted products, depending on the N-substituents. The dimerised 2,2'-bipyrrolidine derivatives with a central carbon-carbon single bond are stable and can be oxidised chemically or electrochemically. These dimers, which are air and moisture-stable, can serve as a source of two electrons in various chemical transformations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Nicolas Chrysochos, Sebastian Paetsch, Benedict J. Elvers, Ivo Krummenacher, Muneshwar Nandeshwar, Ganesan Prabusankar, Holger Braunschweig, Carola Schulzke, Prince Ravat, Anukul Jana
Summary: The synthesis of a twisted, push-pull, and electron-rich alkene is reported, providing a unique combination for alkene compounds. This newly synthesized alkene motif was used as a donor for the synthesis of a boron-containing pi-conjugated compound with zwitterionic properties through intramolecular charge transfer.
CHEMICAL COMMUNICATIONS
(2023)